6-Bromo-3-phenyl-imidazo[1,2-a]pyridine → 3-Phenyl-6-(2-p-tolyl-2H-pyrazol-3-yl)-imidazo[1,2-a]pyridine

HRID 629278Notes

Reaction equation

HRID 629278 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:25]2[N:29]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)[N:28]=[CH:27][CH:26]=2)O1>>[C:11]1([C:8]2[N:6]3[CH:7]=[C:2]([C:25]4[N:29]([C:30]5[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=5)[N:28]=[CH:27][CH:26]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 529368446-Bromo-3-phenyl-imidazo[1,2-a]pyridine2×HCID 901892341-(4-methylphenyl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 760725263-Phenyl-6-(2-p-tolyl-2H-pyrazol-3-yl)-imidazo[1,2-a]pyridine

Procedure

The title compound, off-white solid (53 mg, 41%), MS (ISP) m/z=351.5 [(M+H)+], mp 107° C., was prepared in accordance with the general method of example 1 from 6-bromo-3-phenyl-imidazo[1,2-a]pyridine (intermediate G) (0.1 g, 0.366 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-p-tolyl-1H-pyrazole (intermediate C) (0.125 g, 0.44 mmol).

Sources & evidence

ORD record
ord-0bffb08aa61f4a6abcbe8cfd8d8ee268
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

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