Pyridine → HCID 11955084, compound

HRID 1714701Notes

Reaction equation

HRID 1714701 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH2:27])=[CH:17][CH:16]=1.N1C=CC=CC=1.C(OC)(C)(C)C>C1(C)C=CC=CC=1>[F:13][C:14]([F:28])([F:29])[C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:8]([C:7]2[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=2)=[O:9])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15413tert-Butyl methyl etherHCID 2782707HCID 2782707, compoundHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride

Product 1

HCID 11955084HCID 11955084, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 0.29 g of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride was added dropwise to a solution of 0.36 g of 4′-trifluoromethyl-2-aminobiphenyl and 0.18 g of pyridine in 10 ml of toluene, after which the mixture was stirred at room temperature for 16 hours. 30 ml of methyl tert-butyl ether were added, and the organic phase was washed successively with 2% strength hydrochloric acid, 2% strength aqueous sodium hydroxide solution and then with dilute sodium chloride solution. The organic phase was dried and concentrated under reduced pressure. The crude product was stirred with 5 ml of diisopropyl ether. The solid that remained was separated off and dried. This gave 0.45 g of the desired product as a white powder; m.p. 164-165° C.

Workup

  1. washthe organic phase was washed successively with 2% strength hydrochloric acid, 2% strength aqueous sodium hydroxide solution
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. stirringThe crude product was stirred with 5 ml of diisopropyl ether
  5. customThe solid that remained was separated off
  6. customdried

Sources & evidence

ORD record
ord-647a0745bed04e9d9149580db0bff8f0
Source dataset
uspto-grants-2010_09
Patent number
US07799334B2

Reaction notes

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