Water → tert-Butyl(+/-)-cyclopentyl{4-[(3-oxo-1,3-dihydro-2H-indazol-2-yl)methyl]phenyl}acetate

HRID 877236Notes

Reaction equation

HRID 877236 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH:29]1([CH:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:2]3[C:3](=[O:10])[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1]3)=[CH:16][CH:17]=2)[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81829IndazolinoneHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 58136663tert-Butyl(+/-)-cyclopentyl{4-[(3-oxo-1,3-dihydro-2H-indazol-2-yl)methyl]phenyl}acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., 170.9 mg (1.27 mmol) of 1,2-dihydro-3H-indazol-3-one were added to 50.9 mg (1.27 mmol, 60% pure) of sodium hydride in 1.8 ml of DMF. The mixture was stirred for 30 min, and 500 mg (1.06 mmol) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0° C. The reaction mixture was stirred for a further 30 min, and water and ethyl acetate were then added. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by preparative RP-HPLC (mobile phase: acetonitrile/water gradient). This gave 217 mg (50.3% of theory) of the target compound.

Workup

  1. stirringThe reaction mixture was stirred for a further 30 min
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was purified by preparative RP-HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-3789b8d5daec4dd9a5f3c37cf856f1c7
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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