4-(6-Bromoimidazo[1,2-a]pyridin-3-yl)benzonitrile → 4-{6-[2-(4-Trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-imidazo [1,2-a]pyridin-3-yl}-benzonitrile

HRID 629292Notes

Reaction equation

HRID 629292 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:27]2[N:31]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)[N:30]=[CH:29][CH:28]=2)O1>>[F:41][C:38]([F:39])([F:40])[C:35]1[CH:34]=[CH:33][C:32]([N:31]2[C:27]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]5[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=5)=[CH:9][N:10]=4)[CH:7]=3)=[CH:28][CH:29]=[N:30]2)=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 898271504-(6-Bromoimidazo[1,2-a]pyridin-3-yl)benzonitrile2×HCID 901894005-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole2×

Product 1

HCID 760724274-{6-[2-(4-Trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-imidazo [1,2-a]pyridin-3-yl}-benzonitrile

Procedure

The title compound, off-white solid (59 mg, 41%), MS (ISP) m/z=430.6 [(M+H)+], mp 201° C., was prepared in accordance with the general method of example 1 from 4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-benzonitrile (intermediate N) (0.1 g, 0.335 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(4-trifluoromethyl-phenyl)-1H-pyrazole (intermediate P) (0.15 g, 0.44 mmol).

Sources & evidence

ORD record
ord-3183c97aa1b84940a23d2194a378e9c3
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

Loading…