Water → HCID 21183727, compound

HRID 1384826Notes

Reaction equation

HRID 1384826 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13]2.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:22]([O:21][C:19]([C:14]1[NH:15][C:16]2[C:12]([C:13]=1[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][C:10]([F:9])=[CH:18][CH:17]=2)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 20884Ethoxalyl chlorideHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 21183727HCID 21183727, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 40 ml (313 mmol) of ethyl chloroglyoxylate and of 36 ml (313 mmol) of titanium tetrachloride in 1 l of dichloromethane is stirred for 15 min at room temperature. A solution of 50 g (241 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate in dichloromethane is added and the mixture is stirred for 2 h at room temperature. The mixture is poured into water and the organic phase is separated by settling, washed with dilute sodium hydroxide solution and dried over sodium sulphate. 31.5 g (102 mmol) of product are obtained, which product is used as is in the following stage.

Workup

  1. customthe organic phase is separated
  2. washwashed with dilute sodium hydroxide solution
  3. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-3ac19ed775624f80a4baeb34fc8a2821
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

Loading…