6-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine → HCID 86651935, compound

HRID 1684907Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[F:18][C:19]1[C:24]([CH:25]=[O:26])=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:20]4[C:19]([F:18])=[C:24]([CH:23]=[CH:22][CH:21]=4)[CH:25]=[O:26])=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

500 mg of 6-bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 473 mg of 2-fluoro-3-formylbenzeneboronic acid and 93 mg of tetrakis(triphenylphosphine)palladium are placed under a stream of argon in a round-bottomed flask comprising a mixture, degassed beforehand under a stream of argon, of 5 ml of acetonitrile, 5 ml of toluene and 6 ml of a 2M sodium carbonate solution. The reaction mixture is heated at 70° C. for 21 h. After cooling, the reaction mixture is diluted with ethyl acetate and water and then the organic phase is separated, dried and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/ethyl acetate 98/02 mixture. 324 mg of compound are obtained.

Workup

customcomprising a mixture, degassed
temperatureAfter cooling
additionthe reaction mixture is diluted with ethyl acetate and water
customthe organic phase is separated
customdried
customevaporated under reduced pressure
customThe residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record: ord-089286299dae47038d6a6827b80c9220
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148370B2

Reaction notes

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