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

HRID 1399483Notes

Reaction equation

HRID 1399483 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-7034d79099a545cba19a65301d521710
Source dataset
uspto-grants-2014_12
Patent number
US08906633B2

Reaction notes

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