Cesium carbonate → HCID 66855656, compound

HRID 1530106Notes

Reaction equation

HRID 1530106 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]([O:25][CH2:26][CH3:27])=[O:24])=[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.[C:28]1(B2OC(C)(C)C(C)(C)O2)[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O>[C:28]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:12]4[S:13][C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:15]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[N:16]=4)=[C:9]([CH3:11])[N:10]=3)[CH:7]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66856032HCID 66856032, compound

Product 1

HCID 66855656HCID 66855656, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of ethyl 2-(6-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)-4-phenyl-1,3-thiazole-5-carboxylate (267 mg, 0.6 mmol) obtained above in DME (18 mL) and water (3.6 mL), were added 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (250 mg, 1.2 mmol), cesium carbonate (586 mg, 1.8 mmol) and [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (49.1 mg, 0.06 mmol) under a nitrogen atmosphere, and the mixture was stirred at 95° C. for 3 h. The reaction mixture was allowed to cool to rt. The resulting precipitate was collected by filtration and washed with water and diethyl ether to give the title compound (223 mg, 84%) as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-c9d824d7bf6b4e249eb45c049a5d9397
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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