Potassium Carbonate → 1-(propan-2-yl)-4-(2,3,4-trifluorophenyl)-1H-indole-3-carboxaldehyde

HRID 402844ノート

反応式

HRID 402844 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:14]=[O:15])=[CH:5][N:6]2[CH:11]([CH3:13])[CH3:12].[F:16][C:17]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.Cl[Pd]Cl.[Fe]>[CH3:12][CH:11]([N:6]1[C:7]2[C:3](=[C:2]([C:20]3[CH:19]=[CH:18][C:17]([F:16])=[C:22]([F:23])[C:21]=3[F:24])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH:14]=[O:15])=[CH:5]1)[CH3:13]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 772308814-bromo-1-isopropyl-1H-indole-3-carbaldehyde

生成物 1

HCID 866852811-(propan-2-yl)-4-(2,3,4-trifluorophenyl)-1H-indole-3-carboxaldehyde収率 68.7%

試薬・触媒・溶媒 3

HCID 178454869HCID 178454869、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

To a solution of 4-bromo-1-(propan-2-yl)-1H-indole-3-carboxaldehyde (100 mg, 0.376 mmol) and 2,3,4-trifluorophenylboronic acid (79 mg, 0.451 mmol) in dioxane (2 mL) and water (0.5 mL) in a 5 mL microwave reaction vial was added potassium carbonate (156 mg, 1.13 mmol) and dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium (II) (25 mg, 0.038 mmol). The reaction was placed under nitrogen, sealed and heated in a microwave reactor at 140° C. for 15 minutes. The solvent was removed in vacuo and the residue was partitioned with ethyl acetate and aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes) to give the title intermediate (82 mg).

後処理

  1. customsealed
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned with ethyl acetate and aqueous sodium bicarbonate
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (COMBI FLASH 24 gm column, gradient of 0-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-32e07e7475ba49d9b3530fab92a58071
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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