Potassium Carbonate → {1-[4-(3-Phenyl-6-vinyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 872323Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23](Br)=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:41](C([SnH3])=C(CCCC)CCCC)[CH2:42]CC>[Br-].C([N+](CC)(CC)CC)C.C1COCC1>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH:41]=[CH2:42])=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of {1-[4-(6-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (70 mg, 60% purity by UPLC-MS), potassium carbonate (11.2 mg), tetraethylammonium bromide (22.1 mg), tributylvinyl stannane (38.5 mg) and trans-dichlorobis(triphenylphosphine) palladium (II) (1.7 mg) in THF (0.66 mL) under argon was heated at 120° C. for 45 min. On cooling the reaction was partitioned between DCM and water, the organic extract dried and concentrated to give the crude title compound which was used without further purification.

Workup

temperatureOn cooling the reaction
customwas partitioned between DCM and water
extractionthe organic extract
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-d2c280c6d2174654aa5897fb9bdb1fd9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Reaction notes

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