Binap, (A+-)- → HCID 24946165, compound

HRID 1803533Notes

Reaction equation

HRID 1803533 reaction equation
BrC1C=C2C(=CC=1)[C:8](=[O:12])[NH:7][N:6]=C2Cl.[ClH:14].O1[C:19]2[CH:20]=[CH:21][C:22]([NH:24]C)=[CH:23][C:18]=2[CH2:17]C1.C1C=CC(P(C2[C:48]([C:49]3[C:58](P(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:57][CH:56]=[C:55]4[C:50]=3C=C[CH:53]=[CH:54]4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-:76])(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:14][C:17]1[C:18]2[C:19](=[CH:20][CH:21]=[C:22]([NH:24][CH2:48][C:49]3[CH:58]=[CH:57][C:56]4[O:76][CH2:53][CH2:54][C:55]=4[CH:50]=3)[CH:23]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 66706804HCID 66706804, compound

Product 1

HCID 24946165HCID 24946165, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), (2,3-dihydro-benzofuran-5-yl)-methylamine hydrochloride (119 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-[(2,3-dihydro-benzofuran-5-ylmethyl)-amino]-2H-phthalazin-1-one: 25 mg (13.2%): m/z (M+H)=328. 1H-NMR (DMSO-d6) δ: 12.28 (s, 1H), 7.86 (d, 1H), 7.51 (m, 1H), 7.19 (s, 1H), 7.10 (dd, 1H), 7.05 (d, 1H), 6.78 (s, 1H), 6.67 (d, 1H), 4.44 (t, 2H), 4.26 (d, 2H), 3.09 (t, 2H).

Workup

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2091dd3c57f647e6800e52732994b6c7
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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