Reaction #60693

ord-2b638aacce8e4dc78b66860ae6fd61a2

Reaction equation

COc1ccccc1
anisole
CC(C)(C)OC(=O)N1CCC(COCC(NC(=O)c2ccc3c(Cl)c[nH]c3c2)c2ccncc2)CC1
4-{2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-pyridinyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester
→
O=C(NC(COCC1CCNCC1)c1ccncc1)c1ccc2c(Cl)c[nH]c2c1
title compound
Yield 101.4%
O=C(NC(COCC1CCNCC1)c1ccncc1)c1ccc2c(Cl)c[nH]c2c1
3-Chloro-N-[1-(4-pyridinyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide
Yield 101.4%

Reactants

—
crude residue
COc1ccccc1
anisole
CC(C)(C)OC(=O)N1CCC(COCC(NC(=O)c2ccc3c(Cl)c[nH]c3c2)c2ccncc2)CC1
4-{2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-pyridinyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Using deprotection method B, but without addition of anisole, 4-{2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-pyridinyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester (83 mg, 0.16 mmol) afforded 67 mg (100%) of the title compound as a crude residue, which was used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07427632B2uspto-grants-2008_09