A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394

M. Bhupathy; David A. Conlon; Kenneth M. Wells; John R. Nelson; Paul J. Reider; Kai Rossen; Jess W. Sager; R. P. Volante; Bruce D. Dorsey; Jacob M. Hoffman; Sally A. Joseph; Stacey L. Mcdaniel

doi:10.1002/jhet.5570320431

A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394

M. Bhupathy
, David A. Conlon
, Kenneth M. Wells
, John R. Nelson
, Paul J. Reider
, Kai Rossen
, Jess W. Sager
, R. P. Volante
, Bruce D. Dorsey
, Jacob M. Hoffman
, Sally A. Joseph
, Stacey L. Mcdaniel

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L‐754,394, is described. The synthesis was accomplished in ten steps and in 15% overall yield from commercially available methyl 2‐furoate.

Original language	English (US)
Pages (from-to)	1283-1287
Number of pages	5
Journal	Journal of Heterocyclic Chemistry
Volume	32
Issue number	4
DOIs	https://doi.org/10.1002/jhet.5570320431
State	Published - 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1002/jhet.5570320431

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Bhupathy, M., Conlon, D. A., Wells, K. M., Nelson, J. R., Reider, P. J., Rossen, K., Sager, J. W., Volante, R. P., Dorsey, B. D., Hoffman, J. M., Joseph, S. A., & Mcdaniel, S. L. (1995). A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394. Journal of Heterocyclic Chemistry, 32(4), 1283-1287. https://doi.org/10.1002/jhet.5570320431

@article{4d59c051c57c4b2c91b46826e597f70a,

title = "A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394",

abstract = "A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L‐754,394, is described. The synthesis was accomplished in ten steps and in 15\% overall yield from commercially available methyl 2‐furoate.",

author = "M. Bhupathy and Conlon, \{David A.\} and Wells, \{Kenneth M.\} and Nelson, \{John R.\} and Reider, \{Paul J.\} and Kai Rossen and Sager, \{Jess W.\} and Volante, \{R. P.\} and Dorsey, \{Bruce D.\} and Hoffman, \{Jacob M.\} and Joseph, \{Sally A.\} and Mcdaniel, \{Stacey L.\}",

year = "1995",

doi = "10.1002/jhet.5570320431",

language = "English (US)",

volume = "32",

pages = "1283--1287",

journal = "Journal of Heterocyclic Chemistry",

issn = "0022-152X",

publisher = "John Wiley and Sons Inc.",

number = "4",

}

Bhupathy, M, Conlon, DA, Wells, KM, Nelson, JR, Reider, PJ, Rossen, K, Sager, JW, Volante, RP, Dorsey, BD, Hoffman, JM, Joseph, SA & Mcdaniel, SL 1995, 'A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394', Journal of Heterocyclic Chemistry, vol. 32, no. 4, pp. 1283-1287. https://doi.org/10.1002/jhet.5570320431

TY - JOUR

T1 - A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394

AU - Bhupathy, M.

AU - Conlon, David A.

AU - Wells, Kenneth M.

AU - Nelson, John R.

AU - Reider, Paul J.

AU - Rossen, Kai

AU - Sager, Jess W.

AU - Volante, R. P.

AU - Dorsey, Bruce D.

AU - Hoffman, Jacob M.

AU - Joseph, Sally A.

AU - Mcdaniel, Stacey L.

PY - 1995

Y1 - 1995

N2 - A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L‐754,394, is described. The synthesis was accomplished in ten steps and in 15% overall yield from commercially available methyl 2‐furoate.

AB - A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L‐754,394, is described. The synthesis was accomplished in ten steps and in 15% overall yield from commercially available methyl 2‐furoate.

UR - https://www.scopus.com/pages/publications/0029098638

UR - https://www.scopus.com/pages/publications/0029098638#tab=citedBy

U2 - 10.1002/jhet.5570320431

DO - 10.1002/jhet.5570320431

M3 - Article

AN - SCOPUS:0029098638

SN - 0022-152X

VL - 32

SP - 1283

EP - 1287

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 4

ER -

A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394

Abstract

All Science Journal Classification (ASJC) codes

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