Reaction #68321

ord-f48971a9f1bb4eaa98fcd67e13c04404

Reaction equation

CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
Compound 8
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide
O=C([O-])[O-].[K+].[K+]
K2CO3
IC1CCCC1
cyclopentyl iodide
→
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(OC3CCCC3)cc2n1Cc1ccccc1
title compound
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(OC3CCCC3)cc2n1Cc1ccccc1
1-Benzyl-6-(cyclopentoxy)-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

Reactants

CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
Compound 8
CC(C)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(O)cc2n1Cc1ccccc1
1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide
O=C([O-])[O-].[K+].[K+]
K2CO3
IC1CCCC1
cyclopentyl iodide

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following General Procedure A, 1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide (Compound 8, 40 mg, 0.092 mmol) in DMF (1.0 ml) was reacted with K2CO3 (38 mg, 0.28 mmol), cyclopentyl iodide (53 μl, 0.46 mmol) to yield the title compound as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524917B2uspto-grants-2013_09