1-Bromopentane → 1-Pentyl-1H-indole-3-carboxylic acid

HRID 55929

反応式

HRID 55929 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:2]=1)([OH:12])=[O:11]

参加物

5

反応物 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 69867Indole-3-Carboxylic Acid

生成物 1

HCID 173817231-Pentyl-1H-indole-3-carboxylic acid収率 49%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Indole 3-carboxylic acid (3 g, 18.62 mmol) was added to a suspension of sodium hydride (60% in oil) (1.11 g, 1.5 eq) in dry DMF (30 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for 45 min (H2 evolving has ceased) and to this was added 1-bromopentane (4.62 ml, 2 eq) in dry DMF (10 ml) dropwise. The mixture was stirred at room temperature overnight. The solvents were removed in vacuo and to the residue was added water (30 ml) and ethyl acetate (30 ml). The ethyl acetate portion was separated, dried over sodium sulphate, filtered and evaporated to dryness. The crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane) to give the title compound (2.12 g, 49%) as a cream solid.

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe solvents were removed in vacuo and to the residue
  3. additionwas added water (30 ml) and ethyl acetate (30 ml)
  4. customThe ethyl acetate portion was separated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-574280e64f424f10aa4edb28f666fb6a
出典データセット
uspto-grants-2016_09
特許番号
US09434687B2

関連ノート

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