4-Methylpyrazole → HCID 57762805, compound

HRID 230703Notes

Reaction equation

HRID 230703 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Cl[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19]([C:26]([F:29])([F:28])[F:27])=[N:18]2)=[CH:13][CH:12]=1>CN(C=O)C>[CH3:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=4[C:19]([C:26]([F:29])([F:27])[F:28])=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 34064-MethylpyrazoleHCID 24758Sodium hydrideHCID 509927231-[4-(chloromethyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 57762805HCID 57762805, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% in mineral oil, 10.0 mg; 0.25 mmol) was added in one portion to a room temperature stirring solution of 4-methyl-1H-pyrazole (15.0 mg; 0.18 mmol) in anhydrous DMF (1 mL). After stirring at this temperature for 15 minutes, a solution of 1-[4-(chloromethyl)phenyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (52.0 mg; 0.16 mmol) in anhydrous DMF (1 mL) was added and the resulting mixture stirred at room temperature for a further 23 hours. The reaction was quenched with aqueous hydrochloric acid (2M; 1 mL), concentrated in vacuo and purified by MDAP, giving the title compound (35.6 mg; 60%).

Workup

  1. stirringthe resulting mixture stirred at room temperature for a further 23 hours
  2. customThe reaction was quenched with aqueous hydrochloric acid (2M; 1 mL)
  3. concentrationconcentrated in vacuo
  4. custompurified by MDAP

Sources & evidence

ORD record
ord-67f48c4921164111b10ddaab85768bdc
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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