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

HRID 55929

Reaction equation

HRID 55929 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-574280e64f424f10aa4edb28f666fb6a
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Linked notes

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