Sodium Carbonate → 1-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehyde

HRID 402819ノート

反応式

HRID 402819 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:17]([CH3:19])[CH3:18])[CH:12]=[C:11]2[CH:20]=[O:21].[F:22][C:23]1[C:28]([F:29])=[C:27]([F:30])[CH:26]=[CH:25][C:24]=1B(O)O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:18][CH:17]([N:13]1[C:14]2[C:10](=[CH:9][C:8]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[C:28]([F:29])[C:27]=3[F:30])=[CH:16][CH:15]=2)[C:11]([CH:20]=[O:21])=[CH:12]1)[CH3:19]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 50503775-Bromo-1-(1-methylethyl)-1H-indole-3-carboxaldehyde

生成物 1

HCID 866852731-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehyde収率 83.8%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Sodium carbonate (0.188 mL, 2M, 0.376 mmol) was added to a stirred room temperature solution of 5-bromo-1-(propan-2-yl)-1H-indole-3-carbaldehyde (50 mg, 0.188 mmol), 2,3,4-trifluorophenylboronic acid (66 mg, 0.376 mmol) and PdCl2(dppf) (13.7 mg, 0.019 mmol) in DMF (1.0 mL) and the reaction mixture was stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature, partitioned between ethyl acetate (2×15 mL) and water (10 mL), washed with saturated sodium bicarbonate (10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (50 mg).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (2×15 mL) and water (10 mL)
  3. washwashed with saturated sodium bicarbonate (10 mL), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-910940917b6342969e7c05a6841a63c2
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

反応ノート

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