Thionyl Chloride → 3-chlorocarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole hydrochloride

HRID 1869175Notes

Reaction equation

HRID 1869175 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:18]3[CH:25]=[CH:24][N:23]([CH3:26])[C:19]=3[N:20]=[CH:21][N:22]=2)[CH:9]=1)(O)=[O:6]>>[ClH:3].[Cl:3][C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:18]3[CH:25]=[CH:24][N:23]([CH3:26])[C:19]=3[N:20]=[CH:21][N:22]=2)[CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689701693-carboxy-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole

Product 1

HCID 865948063-chlorocarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole hydrochloride

Procedure

6 cm3 of thionyl chloride are added to 0.9 g (3.08 mmol) of 3-carboxy-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole at a temperature in the region of 20° C. under an argon atmosphere. After stirring under reflux for 2 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), triturated twice successively with 30 cm3 of dichloromethane and then concentrated to dryness under reduced pressure (2.7 kPa), giving 0.92 g of 3-chlorocarbonyl-1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-indole hydrochloride in the form of a yellow powder, which is used directly in the following step.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customtriturated twice successively with 30 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-d6a295153bca46af8eb415efc96077d1
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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