Methyl iodide → HCID 86700251, compound

HRID 879442Notes

Reaction equation

HRID 879442 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:33]=[C:32]5[C:28]([C:29]([F:34])=[N:30][NH:31]5)=[CH:27][CH:26]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:45](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:33]=[C:32]5[C:28]([C:29]([F:34])=[N:30][N:31]5[CH3:45])=[CH:27][CH:26]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:38]1[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 178472574HCID 178472574, compound

Product 1

HCID 86700251HCID 86700251, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3-fluoro-1H-indazol-6-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (39.7 mg, 0.0631 mmol) and cesium carbonate (62 mg, 0.189 mmol) in anhydrous DMF (1.0 mL) at 0° C. was added iodomethane (5.9 μL, 0.0947 mmol) and reaction stirred for 1 h. More iodomethane (3.0 μL) was added and reaction was stirred for 30 minutes, and stored in freezer overnight. Reaction mixture was diluted with ethyl acetate, washed with 5% lithium chloride solution (3×), brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 40% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C35H33ClFN4O3S: 643.2 (M+H+); Found: 643.2 (M+H+).

Workup

  1. additionwas added
  2. customreaction
  3. stirringwas stirred for 30 minutes
  4. waitstored in freezer overnight
  5. customReaction mixture
  6. washwashed with 5% lithium chloride solution (3×), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by CombiFlash (0 to 40% EtOAc/Hex)
  11. customto give product

Sources & evidence

ORD record
ord-9e58316688ad4d2eb17ebf979173506a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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