6-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine → 3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-4-fluorobenzaldehyde

HRID 1684919ノート

反応式

HRID 1684919 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[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[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[CH:21]=[C:22]([CH:23]=[CH:24][C:19]=4[F:18])[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 2763240(2-Fluoro-5-formylphenyl)boronic acid

生成物 1

HCID 866519373-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-4-fluorobenzaldehyde収率 53.3%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
75 °C

実験手順

800 mg of 6-bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine, 437 mg of 2-fluoro-5-formylbenzeneboronic acid and 150 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 8 ml of acetonitrile, 8 ml of toluene and 10 ml of a 0.5M sodium carbonate solution. The mixture is heated at 75° C. for 5 hours and then diluted, after cooling, with a mixture of water and ethyl acetate. The organic phase is separated, dried and concentrated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/ethyl acetate mixture. 486 mg of compound are obtained.

後処理

  1. customcomprising a mixture, degassed
  2. additiondiluted
  3. temperatureafter cooling, with a mixture of water and ethyl acetate
  4. customThe organic phase is separated
  5. customdried
  6. concentrationconcentrated 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-61f863bbe91b42948ae28152cc2f65cc
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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