Methyl iodide → HCID 57762820, compound

HRID 230705Notes

Reaction equation

HRID 230705 reaction equation
[H-].[Na+].[F:3][C:4]([F:29])([F:28])[C:5]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])=[CH:16][CH:15]=2)[N:6]=1.[CH3:30]I>CN(C=O)C>[CH3:30][N:20]([C:17]1[CH:16]=[CH:15][C:14]([N:7]2[C:8]3[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=3[C:5]([C:4]([F:3])([F:28])[F:29])=[N:6]2)=[CH:19][CH:18]=1)[C:21]([N:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57762788HCID 57762788, compound

Product 1

HCID 57762820HCID 57762820, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an inert atmosphere (Ar), NaH (60% in mineral oil, 3.8 mg; 95 μmol) was added in one portion to a stirring solution of N-{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}-1-pyrrolidinecarboxamide (17.7 mg; 44 μmol) in anhydrous DMF (1.5 mL). After stirring at room temperature for 1 hour, MeI (20 μL; 0.32 mmol) was added in one portion, and the reaction stirred at this temperature for 2 hours 10 minutes. The reaction was quenched with methanolic ammonia (1M, 1 mL), concentrated in vacuo and purified by column chromatography, giving the desired material as a yellow oil (15.4 mg; 84%).

Workup

  1. stirringthe reaction stirred at this temperature for 2 hours 10 minutes
  2. customThe reaction was quenched with methanolic ammonia (1M, 1 mL)
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-ae0a9dbadf8b4e9eb7f30fe0613ddcf6
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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