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

HRID 1677684Notes

Reaction equation

HRID 1677684 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-e41f226dbe4e4507ab63d5255e655d25
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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