Methyl iodide → HCID 66815815, compound

HRID 1697091Notes

Reaction equation

HRID 1697091 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[C:13]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.CI.[C:28]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH3:18][C:15]1[N:14]=[C:13]([NH:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:12]([C:10](=[O:11])[CH2:9][CH2:8][C:5]2[CH:6]=[N:7][C:2]([S:1][CH3:28])=[CH:3][CH:4]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178425703HCID 178425703, compound

Product 1

HCID 66815815HCID 66815815, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

3-(6-Mercaptopyridin-3-yl)-1-(6-methyl-2-phenylaminopyridin-3-yl)-propan-1-one (0.4 g) was dissolved in DMF (5 mL), and methyl iodide (0.05 mL) added, followed by K2CO3 (0.138 g). The reaction mixture was allowed to stand at RT for 2.5 h, then worked up in EtOAc/H2O. The organic layer was washed with LiCl (2×, 0.3 wt % aq), dried over MgSO4, filtered, concentrated, and chromatographed over silica (12 g, 1:2 EtOAc/hexane) to provide 1-(6-methyl-2-phenylamino-pyridin-3-yl)-3-(6-methylsulfanyl-pyridin-3-yl)-propan-1-one (0.23 g). M+H=264.

Workup

  1. washThe organic layer was washed with LiCl (2×, 0.3 wt % aq)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed over silica (12 g, 1:2 EtOAc/hexane)

Sources & evidence

ORD record
ord-9739cc486ccd45b8a253e9e4a1bdf81b
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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