4-(Trifluoromethoxy)benzylamine → HCID 24948343, compound

HRID 1803565Notes

Reaction equation

HRID 1803565 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].FC(F)(F)O[C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH3:73][C:74]([O-:77])([CH3:76])[CH3:75].[Na+]>CC(N(C)C)=O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:74]([O:77][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][N:6]=[C:5]3[Cl:13])=[CH:19][CH:18]=1)([CH3:76])([CH3:75])[CH3:73]

Participants

8

Reactant 4

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948343HCID 24948343, compoundYield 17.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 4-(trifluoromethoxy)benzylamine (0.098 mL, 0.642 mmol), Pd2(dba)3 (50 mg, 0.055 mmol), rac-BINAP (112 mg, 0.180 mmol) and NaOtBu (151 mg, 1.571 mmol) in DMA (5 mL) was heated at 85° C. for 2 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat. aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 6-(4-tert-butoxy-benzylamino)-4-chloro-2H-phthalazin-1-one (37 mg) as a beige solid, 1H (400 MHz, d6-DMSO) δ: 4.47 (d, 2H), 6.81 (s, 1H), 7.16 (dd, 1H), 7.35 (d, 2H), 7.50 (d, 2H), 7.69 (t, 1H), 7.93 (d, 1H), 12.35 (s, 1H) ppm; m/z (M+1) 369.93.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat. aq. NaHCO3, brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-587465a039714534bd030807272fd51b
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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