2-Amino-5-bromopyridine-3-carbonitrile → 2-Amino-5-[7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-nicotinonitrile

HRID 269277Notes

Reaction equation

HRID 269277 reaction equation
[F:1][CH:2]([F:24])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[CH:13])=[C:7]2[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:4]=1.[NH2:25][C:26]1[N:33]=[CH:32][C:31](Br)=[CH:30][C:27]=1[C:28]#[N:29]>>[NH2:25][C:26]1[N:33]=[CH:32][C:31]([C:13]#[C:12][C:11]2[CH:10]=[N:9][N:8]3[C:3]([CH:2]([F:1])[F:24])=[CH:4][C:5]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=4)=[N:6][C:7]=23)=[CH:30][C:27]=1[C:28]#[N:29]

Participants

3

Reactant 2

HCID 242291992-Amino-5-bromopyridine-3-carbonitrileHCID 866080343-Ethynyl-7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670008262-Amino-5-[7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-nicotinonitrile

Procedure

The title compound was prepared from 7-difluoromethyl-3-ethynyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.2) (340 g, 1.0 mmol) and 2-amino-5-bromo-nicotinonitrile (example C.23 step 1) (200 mg, 1.0 mmol) according to general procedure II. Obtained as a yellow solid (240 mg, 52%). MS (ISP) 455.3 [(M+H)+]; mp 255° C.

Sources & evidence

ORD record
ord-952f4ea9747f4425b97596fb9ed58ba8
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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