Potassium Carbonate → methyl 5-[4-(1-acetylpiperidin-4-yl)phenyl]-6-chloro-1H-indole-3-carboxylate

HRID 1054719ノート

反応式

HRID 1054719 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]([C:21]1[C:29]2[C:24](=[CH:25][C:26]([Cl:38])=[C:27](B3OCC(C)(C)CO3)[CH:28]=2)[NH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[C:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]3[CH:28]=[C:29]4[C:24](=[CH:25][C:26]=3[Cl:38])[NH:23][CH:22]=[C:21]4[C:19]([O:18][CH3:17])=[O:20])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)(=[O:16])[CH3:15]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 842096201-(4-(4-Bromophenyl)piperidin-1-yl)ethanoneHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate

生成物 1

HCID 86698718methyl 5-[4-(1-acetylpiperidin-4-yl)phenyl]-6-chloro-1H-indole-3-carboxylate収率 83.4%

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

To a solution of 1-[4-(4-bromophenyl)piperidin-1-yl]ethanone (200 mg, 0.70 mmol) in 1,4-dioxane/H2O (5 mL/1 mL) was added methyl-6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (183 mg, 1.20 mmol), potassium carbonate (270 mg, 2.10 mmol) and PddppfCl2 (50 mg, 0.070 mmol). The reaction mixture was degassed with nitrogen and the mixture was heated to 90° C. for 30 minutes. The reaction was concentrated under reduced pressure to give a crude product. The material was partitioned between water (20 mL) and ethyl acetate (20 mL). The layers were separated and the aqueous layer was washed two additional times with ethyl acetate (30 mL). The combined organics layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to to give the title compound (240 mg, 83% yield) which was used in the next step without further purification.

後処理

  1. customThe reaction mixture was degassed with nitrogen
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customto give a crude product
  4. customThe material was partitioned between water (20 mL) and ethyl acetate (20 mL)
  5. customThe layers were separated
  6. washthe aqueous layer was washed two additional times with ethyl acetate (30 mL)
  7. dry with materialThe combined organics layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e6f6a96c841a405c80f17b1911396c95
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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