Anisole → 3-Chloro-N-[1-(4-pyridinyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

HRID 32415Notes

Reaction equation

HRID 32415 reaction equation
C1(OC)C=CC=CC=1.C(OC([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH:25]([NH:32][C:33]([C:35]2[CH:43]=[C:42]3[C:38]([C:39]([Cl:44])=[CH:40][NH:41]3)=[CH:37][CH:36]=2)=[O:34])[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:18][CH2:17]1)=O)(C)(C)C>>[Cl:44][C:39]1[C:38]2[C:42](=[CH:43][C:35]([C:33]([NH:32][CH:25]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH2:24][O:23][CH2:22][CH:19]3[CH2:18][CH2:17][NH:16][CH2:21][CH2:20]3)=[O:34])=[CH:36][CH:37]=2)[NH:41][CH:40]=1

Participants

3

Reactant 2

HCID 7519AnisoleHCID 693106084-(2-[(3-chloro-1H-indole-6-carbonyl)amino]-2-(4-pyridinyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693106063-Chloro-N-[1-(4-pyridinyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamideYield 101.4%

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.

Sources & evidence

ORD record
ord-2b638aacce8e4dc78b66860ae6fd61a2
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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