Reaction #68319

ord-2dce8fcb172c461d969997a417d115a1

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
CCCCCCI
1-iodohexane
→
CCCCCCOc1ccc2c(C(=O)NCc3ccc(F)c(F)c3)c(C(C)C)n(Cc3ccccc3)c2c1
title compound
CCCCCCOc1ccc2c(C(=O)NCc3ccc(F)c(F)c3)c(C(C)C)n(Cc3ccccc3)c2c1
1-Benzyl-N-(3,4-difluorobenzyl)-6-(hexoxy)-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
CCCCCCI
1-iodohexane

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, 10.7 mg, 0.025 mmol) in DMF (1.0 ml) was reacted with K2CO3 (10.0 mg, 0.074 mmol) and 1-iodohexane (18.0 μl, 0.12 mmol) to yield the title compound as a white solid.

Source

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