4-(Trifluoromethyl)phenylboronic acid → 6-(4-Trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-8-carbonitrile

HRID 558606Notes

Reaction equation

HRID 558606 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]([C:11]#[N:12])[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 670011736-Bromoimidazo[1,2-a]pyridine-8-carbonitrile

Product 1

HCID 670002226-(4-Trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-8-carbonitrileYield 59.7%

Procedure

Prepared from 6-bromo-imidazo[1,2-a]pyridine-8-carbonitrile (example C.23 step 2) (1.6 g, 7 mmol) and commercially available 4-trifluoromethylphenylboronic acid (1.505 g, 36 mmol) as described in example C.20 step 2. Obtained the title compound as a white solid (1.2 g, 46%). MS (ISP) 288.0 [(M+H)+].

Sources & evidence

ORD record
ord-603d8fc3ef32431e8dc0712b09b9f05f
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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