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Binap, (A+-)- → HCID 24946522, compound

HRID 1667434
Notes
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Reaction equation

HRID 1667434 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:26]=[CH:25][CH:24]=[CH:23][C:20]=2[CH2:21][NH2:22])[CH:18]=[CH:17][CH:16]=[N: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:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 70150362-(1H-Pyrazol-1-yl)benzylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Product 1

HCID 24946522HCID 24946522, compound

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 31374DimethylacetamideSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2-pyrazol-1-yl-benzylamine (111 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (108 mg, 0.17 mmol) and NaOt-Bu (140 mg, 1.45 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-pyrazol-1-yl-benzylamino)-2H-phthalazin-1-one: 46 mg (22.5%): m/z (M+H)=352. 1H-NMR (DMSO-d6) δ: 12.34 (s, 1H), 8.13 (d, 1H), 7.90 (d, 1H), 7.78 (d, 1H), 7.59 (m, 1H), 7.50 (m, 1H), 7.43 (m, 3H), 7.05 (d, 1H), 6.68 (s, 1H), 6.54 (t, 1H), 4.38 (d, 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-1c8314e3141e4f9681b5c7a2118d9d73
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044041B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes