Cesium carbonate → HCID 66855230, compound

HRID 1530099Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[S:13][C:14]([C:23]4[N:27]=[CH:26][N:25]([CH:28]5[CH2:33][CH2:32][CH2:31][CH2:30][O:29]5)[N:24]=4)=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=3)=[C:9]([CH3:11])[N:10]=2)[CH:7]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][C:41]=1[O:42][CH3:43].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>COCCOC.O.CCOC(C)=O>[CH3:34][O:35][C:36]1[CH:37]=[C:38]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:12]4[S:13][C:14]([C:23]5[N:27]=[CH:26][N:25]([CH:28]6[CH2:33][CH2:32][CH2:31][CH2:30][O:29]6)[N:24]=5)=[C:15]([C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=5)[N:16]=4)=[C:9]([CH3:11])[N:10]=3)[CH:7]=2)[CH:39]=[CH:40][C:41]=1[O:42][CH3:43]

Participants

Conditions

Temperature: 95 °C

Procedure

To a suspension of 6-bromo-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}imidazo[1,2-a]pyridine (157 mg, 0.3 mmol) obtained above in DME (10 mL) and water (2 mL), were added (3,4-dimethoxyphenyl)boronic acid (81.9 mg, 0.45 mmol), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (24.5 mg, 0.03 mmol) and cesium carbonate (293 mg, 0.9 mmol) under a nitrogen atmosphere, and the mixture was stirred at 95° C. for 1 h. The reaction mixture was allowed to cool to rt, and then were added saturated aqueous solution of sodium bicarbonate (30 mL) and EtOAc (50 mL). The resulting precipitate was collected by filtration and washed with THF and diethyl ether to give the title compound (142 mg, 81%) as a white solid.

Workup

temperatureto cool to rt
filtrationThe resulting precipitate was collected by filtration
washwashed with THF and diethyl ether

Sources & evidence

ORD record: ord-5ac8e7519b554c50a2a32b8a72580b57
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090601B2

Reaction notes

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