Methyl iodide → HCID 11210694, compound

HRID 1816874Notes

Reaction equation

HRID 1816874 reaction equation
[CH3:1][C:2]1([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[C:8]2[CH:9]=[C:10]([C:13]3[NH:17][C:16]([C:18]#[N:19])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:20])[CH2:4][O:3]1.[C:26](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[CH3:26][N:17]1[C:13]([C:10]2[CH:11]=[CH:12][C:7]3[NH:6][C:5](=[O:20])[CH2:4][O:3][C:2]([CH3:1])([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[C:8]=3[CH:9]=2)=[CH:14][CH:15]=[C:16]1[C:18]#[N:19]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11325538HCID 11325538, compound

Product 1

HCID 11210694HCID 11210694, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-[5-methyl-2-oxo-5-(2-thienyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl]-1H-pyrrole-2-carbonitrile (0.1 g, 0.29 mmol) in anhydrous DMF (5 mL) at rt under nitrogen was added potassium carbonate (1 g, 7.23 mmol) and iodomethane (0.5 mL, 8 mmol). The reaction mixture was stirred for 2 h and treated with brine (30 mL). Ethyl acetate (50 mL) was added and organic layer separated, dried (Mg2SO4), and concentrated. The residue was purified by a flash chromatography on a silica gel column (hexane:ethyl acetate/2:1) to afford the title compound as a white solid (23 mg, 22%): mp 197-198° C.; 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 7.55 (d, J=4.8, 1H), 7.43 (dd, J=8.4, 1.8 Hz, 1H), 7.35 (d, J=1.8 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.01 (d, J=4.1 Hz, 1H), 6.98 (d, J=4.9 Hz, 1H), 6.93 (d, J=3.0 Hz, 1H), 6.31 (d, J=4.1 Hz, 1H), 4.21 (d, J=15.9 Hz, 1H), 4.07 (d, J=15.9 Hz, 1H), 3.65 (s, 3H), 2.04 (s, 3H). MS (ES) m/z 362 ([M−H]−, 100%).

Workup

  1. customorganic layer separated
  2. dry with materialdried (Mg2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by a flash chromatography on a silica gel column (hexane:ethyl acetate/2:1)

Sources & evidence

ORD record
ord-9dffb0c6867a4d7d9233488ccf69683c
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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