Water → 2-ethyl-5-fluoro-1H-indole

HRID 1751795Notes

Reaction equation

HRID 1751795 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[NH2:12])#[C:2][CH2:3][CH3:4].O>CN1CCCC1=O>[CH2:3]([C:2]1[NH:12][C:6]2[C:5]([CH:1]=1)=[CH:10][C:9]([F:11])=[CH:8][CH:7]=2)[CH3:4]

Participants

4

Reactant 2

HCID 962WaterHCID 580803722-But-1-ynyl-4-fluorophenylamine

Product 1

HCID 205171722-ethyl-5-fluoro-1H-indoleYield 83.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Under argon 4.9 g potassium-tert-butoxide are suspended in 25 ml N-methyl-2-pyrrolidinone and a suspension of 3.4 g 2-but-1-ynyl-4-fluorophenylamine in 25 ml N-methyl-2-pyrrolidinone is added dropwise thereto. The reaction mixture is stirred for 3 hours at ambient temperature and mixed with water. The product is extracted with diethyl ether and purified by chromatography (silica gel, cyclohexane/ethyl acetate 100/0-90/10). 2.83 g product are obtained in the form of a solid. 1H NMR (400 MHz, DMSO): 2.72 (2H, q); 1.27 (3H, t).

Workup

  1. additionis added dropwise
  2. extractionThe product is extracted with diethyl ether
  3. custompurified by chromatography (silica gel, cyclohexane/ethyl acetate 100/0-90/10)

Sources & evidence

ORD record
ord-0d0c4b3599d04e63a7999c9a64a9e5f7
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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