Binap, (A+-)- → HCID 24948533, compound

HRID 1803557Notes

Reaction equation

HRID 1803557 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].[C:14]1([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH2:23][NH2:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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.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]>[C:20]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[C:22]([CH2:23][NH:24][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:21]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 27603683-(Aminomethyl)biphenylHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948533HCID 24948533, compoundYield 2.3%

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (95 mg, 0.366 mmol), 3-phenylbenzylamine (95 mg, 0.518 mmol), Pd2(dba)3 (40 mg, 0.044 mmol), rac-BINAP (76 mg, 0.122 mmol) and NaOtBu (101 mg, 1.05 mmol) in DMA (5 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 6-[(biphenyl-3-ylmethyl)-amino]-4-chloro-2H-phthalazin-1-one (3 mg) as an off white solid, 1H (400 MHz, CDCl3) δ: 4.49 (s, 2H), 7.00 (m, 2H), 7.50 (m, 9H), 8.05 (d, 1H), 10.87 (s, 1H) ppm; m/z (M+1) 361.95.

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-daac9109d5d94b8397c1119410572d16
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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