Lithium Hydroxide → HCID 68279036, compound

HRID 508205Notes

Reaction equation

HRID 508205 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[O:19][CH2:18]3)=[N:7]1)=[O:5].[Li+].[OH-].[CH:35]1[CH:40]=[CH:39][C:38](CBr)=[CH:37][CH:36]=1.C1C[O:46][CH2:45]C1>O.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:23]=[CH:22][C:21]([C:20]([O:19][CH2:18][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:24])=[C:17]([CH2:45][OH:46])[CH:16]=2)=[N:7]1)=[O:5]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 68350592HCID 68350592, compound

Product 1

HCID 68279036HCID 68279036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)isobenzo furan-1(3H)-one (G-2) (0.6 g, 1.32 mmol) and LiOH (0.16 g, 6.58 mmol) in THF (6 mL) and H2O (3 mL) was stirred at rt for 3 h. The solvent was removed under reduced pressure, and the residue was dissolved in DMF (10 mL), followed by the addition of BnBr (0.78 mL, 6.6 mmol). The resulting mixture was stirred at rt for 3 h. The mixture was diluted with H2O, and EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography (PE:EA=4:1) to give the title compound as a colorless oil. LCMS (ESI) calc'd for C30H19ClF5N2O3 for [M+H]+: 585. found: 585.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (10 mL)
  3. stirringThe resulting mixture was stirred at rt for 3 h
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (PE:EA=4:1)

Sources & evidence

ORD record
ord-c9ea905a46bc499ebb981fcbca4dbbf3
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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