Dimethylformamide → 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid chloride

HRID 2382938Notes

Reaction equation

HRID 2382938 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([Cl:23])=[O:19])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 581387741-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Product 1

HCID 581388741-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.400 g, 1.56 mmol) in CH2Cl2 (5 mL) at room temperature was added oxalyl chloride (0.86 mL, 1.7 mmol) followed by DMF (20 μL). Gas evolution was observed. After 30 minutes, the solution was concentrated in vacuo to afford 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid chloride which was used without further purification.

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6c8abf9b1eaa4ef1bdae335d11c32f71
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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