Sodium hydride → HCID 10116214, compound

HRID 1179146Notes

Reaction equation

HRID 1179146 reaction equation
[H-].[Na+].[NH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>CN(C=O)C.CCOC(C)=O>[C:9]1([C:6]2[C:5]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=3)=[C:4]([NH:3][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[O:8][N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 62325Isobutyryl chlorideHCID 10294500HCID 10294500, compound

Product 1

HCID 10116214HCID 10116214, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (18 mg 0.45 mmol) is added to the solution of 2-[4-(5-Amino-3-phenyl-isoxazol4-yl)-phenyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol in DMF at 0° C. under argon atmosphere. The reaction mixture is stirred at room temperature under argon atmosphere for 30 minutes before adding isobutyryl chloride (23.8 ul, 0.23 mmol). The solution is allowed to stir for 8 hours and diluted with EtOAc. The organic layer is washed with H2O brine and dried over MgSO4. Concentration and purification by preparative TLC afford the title compound. 1HNMR 1.11 (s, 3H), 1.12 (s, 3H), 2.60 (m, 1H), 7.26 (d, 2H), 7.4 (m, 5H), 7.72 (d, 2H); ESIMS: m/z 471 (M−H).

Workup

  1. stirringto stir for 8 hours
  2. washThe organic layer is washed with H2O brine
  3. dry with materialdried over MgSO4
  4. concentrationConcentration and purification by preparative TLC

Sources & evidence

ORD record
ord-50a3c0d550224b3db1ba010afd290023
Source dataset
uspto-grants-2007_10
Patent number
US07279477B2

Reaction notes

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