Potassium Carbonate → Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate

HRID 535648

反応式

HRID 535648 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:20]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32](=O)[CH2:33]Br)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)(=[O:22])[CH3:21]>C(#N)C>[C:20]([N:23]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][CH2:33][N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)(=[O:22])[CH3:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 197113291-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

生成物 1

HCID 59636762Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate収率 55%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a solution of piperazine-1-carboxylic acid tert-butyl ester (0.750 g, 4.03 mmol) in dry acetonitrile (20 mL) grounded potassium carbonate (0.486 mL, 8.05 mmol) was added followed by the product mixture from Example 38a (1.134 g) and the reaction was heated at 70° C. under argon over night. The acetonitrile was evaporated and DCM and water was added. The layers were separated and the aq phase was extracted with DCM (3×). The combined organic phases were dried (Na2SO4), filtered and evaporated. The crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100) to give 0.823 g (55%) of the title compound.

後処理

  1. additionwas added
  2. customThe acetonitrile was evaporated
  3. additionDCM and water was added
  4. customThe layers were separated
  5. extractionthe aq phase was extracted with DCM (3×)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100)

出典と根拠

ORDレコード
ord-2270defa2db742d6b09fed1e47e2d406
出典データセット
uspto-grants-2014_10
特許番号
US08859534B2

関連ノート

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