Methyl iodide → HCID 59370339, compound

HRID 1848655Notes

Reaction equation

HRID 1848655 reaction equation
[Cl:1][C:2]1[C:18]([C:19]2[CH:20]=[N:21][C:22]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:24]=2[C:25]#[N:26])=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1.[H-].[Na+].I[CH3:36]>CN(C=O)C>[Cl:1][C:2]1[C:18]([C:19]2[CH:20]=[N:21][C:22]([C:27]([F:29])([F:28])[F:30])=[CH:23][C:24]=2[C:25]#[N:26])=[CH:17][C:5]([C:6]([N:8]([C:9]2[C:10]([CH3:16])=[CH:11][CH:12]=[CH:13][C:14]=2[CH3:15])[CH3:36])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68603262HCID 68603262, compound

Product 1

HCID 59370339HCID 59370339, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-(2,6-dimethyl-phenyl)-2-methoxy-benzamide (55.0 mg, 0.12 mmol) in dry DMF (0.5 mL) was added NaH (9.6 mg, 0.32 mmol) and iodomethane (0.15 mL, 0.24 mmol). The mixture was stirred at rt overnight, quenched with 0.5 mL of MeOH and 2 drops of trifluoroacetic acid, and purified via reverse phase preparative LCMS to yield 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-N-(2,6-dimethyl-phenyl)-2-methoxy-N-methyl-benzamide 39-1 (8.3 mg). MS [M+H]+471.1; tR=6.25 min (method 3)

Workup

  1. customquenched with 0.5 mL of MeOH and 2 drops of trifluoroacetic acid
  2. custompurified via reverse phase preparative LCMS

Sources & evidence

ORD record
ord-57dd437a39cb41c5aea82823ae1805cf
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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