Methyl iodide → HCID 59370339, compound

HRID 1486008Notes

Reaction equation

HRID 1486008 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-13a45833271641d085381d8e8bd06a80
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

Loading…