Thionyl Chloride → HCID 21110070, compound

HRID 1766147Notes

Reaction equation

HRID 1766147 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]([OH:22])=O)=[CH:12]2)=[CH:7][CH:6]=1>>[ClH:3].[Cl:3][C:20]([C:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:11]([C:8]2[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=2)[CH:12]=1)=[O:22]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21110059HCID 21110059, compound

Product 1

HCID 21110070HCID 21110070, compound

Procedure

15 cm3 of thionyl chloride were added, at a temperature in the region of 25° C. under an argon atmosphere, to 1.67 g (7 mmol) of 1-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. After stirring at reflux for 2 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa). The residue was 3 times in succession triturated with 20 cm3 of dichloromethane and then concentrated to dryness under reduced pressure (2.7 kPa) to give 1.8 g of 3-chlorocarbonyl-1-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride in the form of a yellow powder which was used directly in the following stage.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  3. customtriturated with 20 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ee9f017b2e3741fc9882de3d01a77dc4
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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