Methyl iodide → HCID 86700284, compound

HRID 879470Notes

Reaction equation

HRID 879470 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[NH:23][CH2:22]4)[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:42].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[N:23]([CH3:42])[CH2:22]4)[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86700285HCID 86700285, compound

Product 1

HCID 86700284HCID 86700284, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxoisoindolin-5-yl)benzo[d]thiazol-6-yl)acetate (94 mg, 0.171 mmol) in DMF (2.0 mL) was added NaH (˜10 mg, 60% oil dispersion) at 0° C. After 15 min, iodomethane (0.016 mL, 0.256 mmol) was added and after 30 min the reaction was allowed to warm to room temperature. Satd. aqueous NH4Cl was added and the reaction was diluted with EtOAc, washed sequentially with 5% aqueous LiCl and brine. The organic layer was dried over Na2SO4, concentrated and purified by flash column chromatography on silica gel using EtOAc to provide the title compound. LCMS-ESI+: calc'd for C31H31ClN2O4S: 563.2 (M+H+); found: 563.2 (M+H+).

Workup

  1. washwashed sequentially with 5% aqueous LiCl and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-59d16eea51e44664a0957755748cb068
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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