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

HRID 1684907노트

반응식

HRID 1684907 반응식
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

참가 물질

4

반응물 2

HCID 8282916-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridineHCID 162178292-Fluoro-3-formylphenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 86651935HCID 86651935, 화합물수율 56.8%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-089286299dae47038d6a6827b80c9220
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148370B2

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