2-Bromopropionitrile → N-{4-[2-(Cyano-methyl-methoxy)-4-fluoro-phenyl]-pyridin-3-yl}-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878031Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:31])[C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)=[C:4]([OH:32])[CH:3]=1.Br[CH:34]([CH3:37])[C:35]#[N:36]>>[C:35]([CH:34]([CH3:37])[O:32][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH3:31])[C:15](=[O:30])[C:16]1[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)#[N:36]

Participants

Reactant 2

HCID 1405382-Bromopropionitrile

HCID 136209610N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 86670703N-{4-[2-(Cyano-methyl-methoxy)-4-fluoro-phenyl]-pyridin-3-yl}-N-methyl-3,5-bis-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 49, from N-[4-(4-fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 48) and 2-bromopropionitrile (CAS RN 19481-82-4). Off-white solid (74%). MS (ESI): m/z =512.0 [M+H]+.

Sources & evidence

ORD record: ord-2390cbe5fe9749e1ac6cf1cc32222f3c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987307B2

Reaction notes

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