Sodium Carbonate → 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine

HRID 1481597Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([C:11]3[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=3)=[N:10][C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:16]([C:14]1[CH:15]=[C:11]([C:9]2[NH:8][C:5]3[CH:6]=[N:7][C:2]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[Cl:21])=[CH:3][C:4]=3[N:10]=2)[N:12]([CH3:20])[N:13]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine (50 mg, 0.15 mmol, prepared as described in the previous step), 2-chlorophenylboronic acid (47 mg, 0.30 mmol), 2M Na2CO3 (0.60 mL, 1.2 mmol) and DME (1 mL) was stirred at 90° C. for 18 h. The resulting mixture was allowed to cool to room temperature and organic layer was separated. The organic layer was purified by direct application to silica preparative TLC plates (2000 micron) and eluted with 3:7 EtOAc-hexanes to yield 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-3H-imidazo[4,5-c]pyridine.

Workup

temperatureto cool to room temperature
customorganic layer was separated
customThe organic layer was purified by direct application to silica preparative TLC plates (2000 micron)
washeluted with 3:7 EtOAc-hexanes

Sources & evidence

ORD record: ord-4636730538744e84b2e68891f0e13031
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409915B2

Reaction notes

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