Binap, (A+-)- → HCID 59743152, compound

HRID 1803555Notes

Reaction equation

HRID 1803555 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].Cl.[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:20]=[CH:21][CH:22]=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:15][CH2:16][C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:20]=[CH:21][CH:22]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 2760945N-[3-(aminomethyl)phenyl]acetamide HydrochlorideHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 59743152HCID 59743152, 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 (100 mg, 0.385 mmol), N-[3-(aminomethyl)phenyl]acetamide hydrochloride (90 mg, 0.448 mmol), Pd2(dba)3 (40 mg, 0.044 mmol), rac-BINAP (81 mg, 0.130 mmol) and NaOtBu (101 mg, 1.05 mmol) in DMA (6 mL) was heated at 80° C. for 3 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 N-{3-[(4-chloro-1-oxo-1,2-dihydro-phthalazin-6-ylamino)-methyl]-phenyl}-acetamide (3 mg) as a light brown solid, 1H (400 MHz, CDCl3) δ: 2.09 (s, 3H), 4.38 (s, 2H), 6.85 (d, 1H), 7.00 (m, 2H), 7.21 (t, 1H), 7.38 (m, 1H), 7.53 (m, 1H), 7.61 (s, 1H), 8.05 (d, 1H), 8.75 (bs, 1H), 10.90 (bs, 1H) ppm; m/z (M+1) 342.98.

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-64f8c4a621aa41a999b565d125a1df8e
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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