1-(4-chlorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-(4-Chloro-2-fluoro-phenyl)-6-[2-(4-chloro-phenyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]pyridine

HRID 629279Notes

Reaction equation

HRID 629279 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[F:18])=[CH:9][N:10]=2)[CH:7]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[N:6]3[CH:7]=[C:2]([C:30]4[N:26]([C:23]5[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=5)[N:27]=[CH:28][CH:29]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)=[C:12]([F:18])[CH:13]=1

Participants

3

Reactant 2

HCID 901893311-(4-chlorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 901894736-Bromo-3-(4-chloro-2-fluorophenyl)imidazo[1,2-a]pyridine2×

Product 1

HCID 760724943-(4-Chloro-2-fluoro-phenyl)-6-[2-(4-chloro-phenyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]pyridine

Procedure

The title compound, white solid (46 mg, 46%), MS (ISP) m/z=423.5 [(M+H)+], mp 148° C., was prepared in accordance with the general method of example 1 from 6-bromo-3-(4-chloro-2-fluoro-phenyl)-imidazo[1,2-a]pyridine (intermediate I) (0.1 g, 0.31 mmol) and 1-(4-chloro-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (intermediate B) (0.11 g, 0.37 mmol).

Sources & evidence

ORD record
ord-8bdb9ad466f2401287bc17350604c26a
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

Loading…