Hydrochloric Acid → HCID 118378868, compound

HRID 931031Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of (8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone (50.0 mg), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (40.0 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (10.5 mg) and cesium carbonate (125 mg) in DME (2.5 mL) was stirred with microwave irradiation at 120° C. for 30 min. To the reaction mixture was added 0.1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (15.6 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-8f5282c99182417bb1208aa45a965113
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296746B2

Reaction notes

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