3,5-Difluorobenzylamine → HCID 24948536, compound

HRID 1667467Notes

Reaction equation

HRID 1667467 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].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([F:23])[CH:22]=1)[CH2:18][NH2:19].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.CC([O-])(C)C.[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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:19][CH2:18][C:17]3[CH:16]=[C:15]([F:14])[CH:22]=[C:21]([F:23])[CH:20]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 1452113,5-DifluorobenzylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948536HCID 24948536, compoundYield 4.8%

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (50 mg, 0.193 mmol), 3,5-difluorobenzylamine (0.026 mL, 0.212 mmol), Pd2(dba)3 (6 mg, 0.0066 mmol), rac-BINAP (18 mg, 0.029 mmol) and NaOt-Bu (46 mg, 0.482 mmol) in DMA (3 mL) was heated at 80° C. for 1.5 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 4-chloro-6-(3,5-difluoro -benzylamino)-2H-phthalazin-1-one (3 mg) as a brown solid, 1H (400 MHz, CDCl3) δ: 4.41 (s, 2H), 6.67 (m, 1H), 6.83 (m, 3H), 6.96 (dd, 1H), 8.10 (d, 1H), 9.58 (s, 1H) ppm; m/z (M+1) 321.98.

Workup

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Sources & evidence

ORD record
ord-7e3f4041707f40ba9912030e656c9f33
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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