Triethylamine → N-(6-Bromo-2-methylpyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748611

Reaction equation

HRID 1748611 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:9])=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.[CH3:17][C:18]1[N:22]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[N:21]=[CH:20][C:19]=1[C:33](Cl)=[O:34]>O1CCCC1>[Br:9][C:5]1[N:6]=[C:7]([CH3:8])[C:2]([NH:1][C:33]([C:19]2[CH:20]=[N:21][N:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][N:24]=3)[C:18]=2[CH3:17])=[O:34])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144180456-Bromo-2-methylpyridin-3-amineHCID 897349975-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

Product 1

HCID 86692559N-(6-Bromo-2-methylpyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-bromo-6-picoline (701 mg) and triethylamine (1.57 ml) in tetrahydrofuran (20 ml) was added 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride (1.34 g) described in Reference Example 180 under ice-cooling, and stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was evaporated, and saturated sodium bicarbonate water was added thereto. The insoluble matter was collected by filtration, washed with water, and then dried in vacuo to give the titled compound as a pale yellow solid (1.66 g). MS (ESI) m/z: 440 (M+H)+.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. additionsaturated sodium bicarbonate water was added
  5. filtrationThe insoluble matter was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ee3c100f965d4379ae4ccacad9c42476
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Linked notes

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