Binap, (A+-)- → HCID 24948154, compound

HRID 1667491Notes

Reaction equation

HRID 1667491 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].[N:14]1([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH2:22][NH2:23])[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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:23][CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[C:19]([N:14]4[CH:18]=[CH:17][CH:16]=[CH:15]4)[CH:20]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 27765333-(1H-Pyrrol-1-Yl)BenzylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24948154HCID 24948154, compoundYield 23.1%

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (160 mg, 0.617 mmol), 3-(1H-pyrol-1-yl)benzylamine (100 mg, 0.581 mmol), Pd2(dba)3 (58 mg, 0.063 mmol), rac-BINAP (116 mg, 0.186 mmol) and NaOtBu (160 mg, 1.665 mmol) in DMA (5 mL) was heated at 85° 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-pyrrol-1-yl-benzylamino)-2H-phthalazin-1-one (47 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 4.49 (d, 2H), 6.26 (t, 2H), 6.87 (s, 1H), 7.19 (dd, 1H), 7.25 (d, 1H), 7.33 (t, 2H), 7.42 (t, 1H), 7.47 (m, 1H), 7.61 (s, 1H), 7.67 (t, 1H), 7.94 (d, 1H), 12.35 (s, 1H) ppm; m/z (M+1) 350.90.

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-0c7478e664a94682a450f3926af3886d
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

Loading…