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

HRID 1684907ノート

反応式

HRID 1684907 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 86651935HCID 86651935、化合物収率 56.8%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-089286299dae47038d6a6827b80c9220
出典データセット
uspto-grants-2012_04
特許番号
US08148370B2

反応ノート

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