Dimethylformamide → 1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride

HRID 2169426Notes

Reaction equation

HRID 2169426 reaction equation
[N:1]1([C:10]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C(Cl)(=O)C([Cl:21])=O.CN(C)C=O>ClCCl>[N:1]1([C:10]2([C:15]([Cl:21])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 867260551-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid

Product 1

HCID 867260561-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid (394) (1.2 g, 5.21 mmol) in dichloromethane (80 mL) was dropwise added oxalyl chloride (1 mL, 11.47 mmol) at 0° C., followed by dimethyl formamide (0.1 mL). The reaction mixture was stirred for 1 h at room temperature. After completion, the reaction mixture is concentrated under argon atmosphere tog et 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride (395) (1.3 g, 100%, crude) as a yellow solid which was directly used for the next step without analysis.

Workup

  1. customat 0° C.
  2. concentrationAfter completion, the reaction mixture is concentrated under argon atmosphere tog et 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride (395) (1.3 g, 100%, crude) as a yellow solid which

Sources & evidence

ORD record
ord-71137298b23c483e98a853a148e34e7d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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