Water → HCID 66794925, compound

HRID 1254462Notes

Reaction equation

HRID 1254462 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].CS[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[C:17](/[CH2:47][CH3:48])=[C:18](\[C:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:41]/[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:36][CH:35]=1)/[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[N:23]=[CH:22]2.[CH2:49](Cl)Cl.O>CO.O>[CH3:49][S:1]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[C:17](/[CH2:47][CH3:48])=[C:18](\[C:34]1[CH:35]=[CH:36][C:37](/[CH:40]=[CH:41]/[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:38][CH:39]=1)/[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[N:23]=[CH:22]2)(=[O:6])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 10313463Potassium peroxymonosulphateHCID 66794924HCID 66794924, compound

Product 1

HCID 66794925HCID 66794925, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Potassium peroxymonosulfate (521 mg, 0.85 mmol) was added to a slurry of (E)-ethyl 3-(4-((E)-2-(2-(methylthio)phenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate (156 mg, 0.28 mmol) in MeOH:H2O (1:1, 6 mL) at room temperature, and the reaction was stirred overnight. DCM and water were added, and the layers were separated. The aqueous layer was washed with DCM (×2). The organic layers were combined, washed with water, washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified on a silica gel column eluted with 0-50% ethyl acetate in hexane affording the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 8.15 (s, 1H), 7.91 (d, 1H), 7.77-7.71 (m, 2H), 7.49-7.46 (m, 3H), 7.41-7.31 (m, 4H), 7.01 (d, 2H), 6.45 (d, 1H), 5.87 (dd, 1H), 4.12 (q, 2H), 3.92-3.85 (m, 1H), 3.82-3.69 (m, 1H), 2.93 (s, 3H), 2.46-2.27 (m, 2H), 2.09-1.97 (m, 3H), 1.85-1.67 (m, 1H), 1.63-1.51 (m, 2H), 1.18 (t, 3H), 0.83 (t, 3H). LCMS: 501 [(M-THP+H)+H]+.

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with DCM (×2)
  3. washwashed with water
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on a silica gel column
  9. washeluted with 0-50% ethyl acetate in hexane affording the title compound

Sources & evidence

ORD record
ord-acf8a2b4669c4e408c0fda6e03c56b99
Source dataset
uspto-grants-2013_06
Patent number
US08455534B2

Reaction notes

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