Thionyl Chloride → 3-chlorocarbonyl-1-(quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride

HRID 1766144Notes

Reaction equation

HRID 1766144 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([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:3][CH:2]=1.S(Cl)([Cl:25])=O>>[ClH:25].[Cl:25][C:20]([C:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[CH:12]=1)=[O:22]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 211100631-(quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 211100743-chlorocarbonyl-1-(quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride

Procedure

50 cm3 of thionyl chloride were added to 3.4 g (11.8 mmol) of 1-(quinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid at a temperature in the region of 20° C. under an argon atmosphere. After stirring at reflux for 2 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa), triturated twice in succession with 30 cm3 of dichloromethane and then concentrated to dryness under reduced pressure (2.7 kPa) to give 11.8 mmol of 3-chlorocarbonyl-1-(quinolin-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 twice in succession with 30 cm3 of dichloromethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-bec6368ce90b49fc98204701d3227d60
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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