1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride → 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide

HRID 640942Notes

Reaction equation

HRID 640942 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.OC=[C:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([C:27]3[CH:28]=[C:29]([NH:33]C(=O)C)[CH:30]=[CH:31][CH:32]=3)=[O:26])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:37]>C1COCC1>[O:37]=[C:17]1[CH2:16][C:24]2[C:19](=[CH:20][C:21]([C:25]([C:27]3[CH:28]=[C:29]([NH:33][C:7]([C:5]4[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=4)=[O:8])[CH:30]=[CH:31][CH:32]=3)=[O:26])=[CH:22][CH:23]=2)[NH:18]1

Participants

4

Reactant 2

HCID 27945811-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chlorideHCID 178474162HCID 178474162, compound

Product 1

HCID 866104001-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A dry 25 mL flask was charged with 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl chloride (0.186 g, 0.873 mmol) and THF (2 mL). 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.200 g, 0.794 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux for 2 h. The reaction mixture was then allowed to cool to room temperature. The room temperature reaction mixture was concentrated in vacuo. The light yellow solids were washed with THF (˜3 mL) and filtered to afford the pure product 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.235 g, 0.627 mmol, 79%).

Workup

  1. temperatureto reflux for 2 h
  2. customThe room temperature reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washThe light yellow solids were washed with THF (˜3 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-da5799ff308744e5acb65678d1fa0961
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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