Methyl iodide → HCID 44608690, compound

HRID 2194550Notes

Reaction equation

HRID 2194550 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:27][CH:26]=2)[CH:5]=[C:6]([F:24])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][N:17]=2)[CH2:12][CH2:11]1.CI.[C:38]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:24][C:6]1[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[N:35]([CH3:38])[N:34]=[N:33][N:32]=3)=[CH:27][CH:26]=2)[CH:3]=[C:2]([F:1])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[CH:18][C:19]([CH2:22][CH3:23])=[CH:20][N:21]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178437152HCID 178437152, compound

Product 1

HCID 44608690HCID 44608690, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example B1 (20 mg, 0.04 mmol) and methyl iodide (10 μL, 0.16 mmol) in DMF (3 mL) is added Cs2CO3 (40 mg, 0.12 mmol). The resulting suspension is heated to 80° C. for 1 h, cooled to rt, and diluted with H2O (20 mL). The mixture is extracted with EtOAc (2×20 mL), and the combined organics are washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by flash chromatography (EtOAc/hexanes gradient) afford the title compounds (Example C1) and (Example C2) as white solids.

Workup

  1. temperaturecooled to rt
  2. extractionThe mixture is extracted with EtOAc (2×20 mL)
  3. washthe combined organics are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-142285754ace48a883b3a03103fbf11a
Source dataset
uspto-grants-2012_12
Patent number
US08334288B2

Reaction notes

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