3-(Bromomethyl)-4-fluorobenzonitrile → 4-{(5-Cyano-2-fluoro-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726229Notes

Reaction equation

HRID 1726229 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:32][C:33]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][C:34]=1[CH2:35]Br>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:35][C:34]2[CH:37]=[C:38]([C:41]#[N:42])[CH:39]=[CH:40][C:33]=2[F:32])[C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrileHCID 68968593HCID 68968593, compound

Product 1

HCID 689717214-{(5-Cyano-2-fluoro-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl esterYield 89.3%

Procedure

Using general procedure H, 4-[4-(4-methoxycarbonyl-phenoxy)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 96) (430 mg, 1.04 mmol) and 2-fluoro-5-cyanobenzyl bromide (289 mg, 1.35 mmol) afforded 4-{(5-cyano-2-fluoro-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester as a white solid (520 mg, 89%).

Sources & evidence

ORD record
ord-12c7a29e58e9491d99511fd5b5619c68
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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