Thionyl Chloride → 5-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carbonyl chloride

HRID 492210Notes

Reaction equation

HRID 492210 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[N:6]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:5]=1)(O)=[O:2].S(Cl)([Cl:26])=O>CN(C)C=O>[Cl:26][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[N:6]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 689708335-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 713779075-Fluoro-1-(quinolin-4-yl)-1H-indole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

20 cm3 of sulphinyl chloride and one drop of dimethylformamide are added at a temperature in the region of 20° C. under an argon atmosphere to 1.53 g (5 mmol) of 3-carboxy-5-fluoro-1-(quinol-4-yl)-1H-indole. After stirring at reflux for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give 1.8 g of 3-chlorocarbonyl-5-fluoro-1-(quinol-4-yl)-1H-indole in the form of a cream solid which is used directly in the following step.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-329bfafc25224e26b5035a03b71be3ef
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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