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/inward/citedby.url?scp=0029098638&partnerID=8YFLogxK

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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