Methyl iodide → HCID 44553732, compound

HRID 1254062Notes

Reaction equation

HRID 1254062 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[N:29][NH:30][N:31]=3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[C:32]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CO.CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[N:29][N:30]([CH3:32])[N:31]=3)=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66986312HCID 66986312, compound

Product 1

HCID 44553732HCID 44553732, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

To the product of Step 1 in 1.5 mL of DMF was added K2CO3 (85 mg, 0.61 mmol). After stirring at rt for 30 min, MeI (0.05 mL, 0.82 mmol) was added and stirring continued for 1.5 h. The reaction mixture was diluted with MeOH/MeCN, and the precipitate was collected by filtration to give the title compound. 1H NMR (500 MHz, (CDCl3): 8.44 (d, 1H), 8.39 (d, 1H), 8.27 (d, 2H), 8.19 (d, 2H), 7.88 (t, 1H), 7.36 (dd, 1H), 7.26 (d, 2H), 7.07 (d, 2H), 4.42 (s, 3H), 4.15 (s, 3H). LCMS: m/z 460 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued for 1.5 h
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8a76efc2eaca4cb891b5351acf778406
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…