Dichloromethane → 1-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carbonyl chloride

HRID 60150Notes

Reaction equation

HRID 60150 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(Cl)Cl.[CH3:10][N:11]1C(C(O)=O)=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=2)[CH:13]=[N:12]1>CN(C)C=O>[CH3:10][N:11]1[C:1]([C:2]([Cl:4])=[O:3])=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=2)[CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 903829831-methyl-4-(6-methyl-2-pyridinyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 903834571-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (0.85 ml) was added to a mixed solution of methylene chloride (5 ml) and N,N-dimethylformamide (5 μl) containing the 1-methyl-4-(6-methylpyridin-2-yl)-1H-pyrazole-5-carboxylic acid (210 mg) obtained in (Example 3.3) <Step 1>, and the obtained mixture was then stirred for 2 hours. Thereafter, the reaction solution was concentrated under reduced pressure to obtain a crude product (230 mg) of the title compound in the form of an orange solid.

Workup

  1. customobtained in (Example 3.3) <Step 1>
  2. concentrationThereafter, the reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93abb11883eb4914b46d4ca62da1a06d
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

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