Methyl iodide → HCID 21865348, compound

HRID 2055949Notes

Reaction equation

HRID 2055949 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[NH:24][C:23](=[O:26])[CH:22]=[N:21]4)[CH:10]=2)=[CH:5][CH:4]=1.[C:29]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[CH3:29][N:24]1[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[O:15][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:27])([F:1])[F:28])=[CH:4][CH:5]=3)[N:14]=[CH:13][N:12]=2)[N:21]=[CH:22][C:23]1=[O:26]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21865040HCID 21865040, compound

Product 1

HCID 21865348HCID 21865348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-1H-quinoxalin-2-one, (Example 32(e)), (0.10 g, 0.26 mmol) and K2CO3 (0.043 g, 0.31 mmol, Aldrich) in DMF (1 mL) was added iodomethane (0.019 mL, 0.31 mmol, Aldrich). The mixture was stirred at room temperature for 20 h, diluted with water and extracted with 25% i-PrOH/CHCl3 (3×). After being concentrated in vacuum, the residue was purified by flash chromatography (0→2% 2M NH3 in MeOH/CH2Cl2) to afford the title compound as an off-white amorphous solid. Mp:158° C. MS (ESI, pos. ion) m/z: 399 (M+1).

Workup

  1. extractionextracted with 25% i-PrOH/CHCl3 (3×)
  2. concentrationAfter being concentrated in vacuum
  3. customthe residue was purified by flash chromatography (0→2% 2M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e86c61a7c5db49189f6b352b8a716ab2
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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