Thionyl Chloride → HCID 21110065, compound

HRID 1766166Notes

Reaction equation

HRID 1766166 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:15]=[C:14]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[C:18]([C:25]([OH:27])=O)=[CH:17]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1>>[ClH:3].[Cl:3][C:25]([C:18]1[C:19]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:16]([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=[C:6]([CH3:5])[CH:15]=2)[CH:17]=1)=[O:27]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21110050HCID 21110050, compound

Product 1

HCID 21110065HCID 21110065, compound

Procedure

15.5 cm3 of thionyl chloride were added, at a temperature in the region of 25° C. under an argon atmosphere, to 1.1 g (3.6 mmol) of 1-(2-methylquinolin-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 twice in succession triturated with 10 cm3 of dichloromethane and the supernatant removed, and then the residue was concentrated to dryness under reduced pressure (2.7 kPa). 1.1 g of 3-chlorocarbonyl-1-(2-methylquinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride were thus obtained in the form of an orange crystalline solid 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 10 cm3 of dichloromethane
  4. customthe supernatant removed
  5. concentrationthe residue was concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-372f5983148941f59f9ef783598a7609
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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