Water → 2-ethyl-6-fluoro-1H-indole

HRID 1640248Notes

Reaction equation

HRID 1640248 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[NH2:12])#[C:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].O>CN1CCCC1=O>[CH2:3]([C:2]1[NH:12][C:6]2[C:5]([CH:1]=1)=[CH:10][CH:9]=[C:8]([F:11])[CH:7]=2)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 581174762-But-1-ynyl-5-fluoro-phenylamine

Product 1

HCID 220222072-ethyl-6-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The reaction was carried out under an argon atmosphere. 21 g (0.13 mol) 2-but-1-ynyl-5-fluoro-phenylamine were added to 30 g (0.27 mol) potassium tert.butoxide in 120 mL N-methyl-2-pyrrolidinone and the mixture was stirred for 4 h at RT. The reaction mixture was mixed with water and extracted with diethyl ether. The organic phase was dried and evaporated down. The residue was purified on silica gel.

Workup

  1. extractionextracted with diethyl ether
  2. customThe organic phase was dried
  3. customevaporated down
  4. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-4c81ad796b964606bfbabfb56d622fe5
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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