Water → tert-Butyl(4-{[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]methyl}phenyl)(cyclopentyl)acetate

HRID 877158Notes

Reaction equation

HRID 877158 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][N:11]=2)=[CH:6][CH:5]=1.[C:21]([O:25][C:26](=[O:41])[CH:27]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[CH:35][CH:34]=1)[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].O>C1COCC1.CN(C=O)C>[C:21]([O:25][C:26](=[O:41])[CH:27]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][N:12]2[N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:20])=[CH:35][CH:34]=1)[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6890844-(4-Chlorophenyl)phthalazin-1-olHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 58136552tert-Butyl(4-{[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]methyl}phenyl)(cyclopentyl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 54 mg (2.14 mmol) of sodium hydride were added a little at a time to a solution of 500 mg (1.95 mmol) of 4-(4-chlorophenyl)phthalazin-1(2H)-one [CAS Reg. No. 51334-86-2] in 7.6 ml of THF. After the evolution of gas had ended, 688 mg (1.95 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate, dissolved in 4.5 ml of DMF, were slowly added dropwise at 0° C., and the reaction solution was then stirred at room temperature overnight. Water was then added carefully to the reaction mixture. The reaction mixture was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase: initially cyclohexane/ethyl acetate 3:1, then ethyl acetate). This gave 630 mg (93% pure, 1.11 mmol, 57% of theory) of a colorless solid.

Workup

  1. additionwere slowly added dropwise at 0° C.
  2. extractionThe reaction mixture was extracted three times with ethyl acetate
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-d5d043e9a235408a9e959f1e03729cfa
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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