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

HRID 55929

반응식

HRID 55929 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 173817231-Pentyl-1H-indole-3-carboxylic acid수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-574280e64f424f10aa4edb28f666fb6a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434687B2

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