Binap, (A+-)- → HCID 67415681, compound

HRID 1803616Notes

Reaction equation

HRID 1803616 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]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][NH2:35])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].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.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:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:34][NH:35][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])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 67418563HCID 67418563, compound

Product 1

HCID 67415681HCID 67415681, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-4-chloro-2H-phthalazin-1-one (140 mg, 0.54 mmol), 4-(2-Aminomethyl-phenyl)-perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (150 mg, 0.49 mmol), Pd2(dba)3 (45 mg, 0.049 mmol), BINAP (92 mg, 0.15 mmol) and NaOt-Bu (138 mg, 1.47 mmol) in DMA (10 mL) was purged with nitrogen for 10 min. The mixture was heated at 90° C. for 5 h. The mixture was allowed to cool and diluted with ethyl acetate (30 mL) and washed with ammonium chloride (25 mL). The organic layer was dried and concentrated. Chromatography on silica yielded the title compound (25 mg, 11%) m/z (M+H)=484.72.

Workup

  1. customwas purged with nitrogen for 10 min
  2. temperatureto cool
  3. additiondiluted with ethyl acetate (30 mL)
  4. washwashed with ammonium chloride (25 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b2b232c3fcc4b4a8987cc3663e843a7
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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