Methanol → HCID 21183741, compound

HRID 1384801Notes

Reaction equation

HRID 1384801 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:2].[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].CO.C[CH:27]([OH:29])C>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13]([C:4]1[N:3]([CH2:1][CH3:2])[C:11]2[C:6]([C:5]=1[C:18](=[O:22])[C:19]([O:29][CH3:27])=[O:20])=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 65578Oxalyl chloride2×HCID 11160681HCID 11160681, compound

Product 1

HCID 21183741HCID 21183741, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 17 g (72 mmol) of ethyl 1-ethyl-5-fluoro-1H-indole-2-carboxylate and of 7.4 ml (84.5 mmol) of oxalyl chloride in 500 ml of toluene is heated at reflux for 6 h. An additional 5 ml (57 mmol) of oxalyl chloride are added, heating is carried out for 1 h at reflux and the mixture is allowed to return to room temperature. 200 ml of methanol are added, the mixture is stirred for 10 min and the solvents are evaporated under reduced pressure. The resulting oil is taken up in dichloromethane and the organic phase is washed with water, dried over magnesium sulphate and concentrated under reduced pressure. After recrystallizing from propan-2-ol, 14 g (43.6 mmol) of compound are obtained in the form of a white solid.

Workup

  1. temperatureat reflux for 6 h
  2. temperatureheating
  3. temperatureat reflux
  4. customto return to room temperature
  5. customthe solvents are evaporated under reduced pressure
  6. washthe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-aa3926f48c084e2496a908d898d43d02
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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