Acetic Acid → HCID 22593733、化合物

HRID 225865

反応式

HRID 225865 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1C=O.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH:13]1([NH:16][C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:15][CH2:14]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 2671641-Methylindole-2-carboxaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 22593733HCID 22593733、化合物収率 69.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1-methylindole-2-carboxaldehyde (1.5 g, 10 mmole), cyclopropylamine (1.14 g, 20 mmole), and glacial acetic acid (0.6 mL, 10 mmole) in MeOH (30 mL) was added NaBH3CN (0.69 g, 11 mmole). The reaction was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 10% NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel (3% MeOWCH2Cl2) gave the title compound (1.3 g. 65%) as a semi-solid: MS (ES) m/e 201 (M+H)+.

後処理

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with 10% NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c494e2b36f35435db665985ce581a063
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

関連ノート

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