Binap, (A+-)- → 4-Chloro-6-(2-chloro-6-phenoxy-benzylamino)-2H-phthalazin-1-one

HRID 1667453

반응식

HRID 1667453 반응식
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:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[CH2:17][NH2:18].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:18][CH2:17][C:16]3[C:19]([O:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:21]=[CH:22][C:15]=3[Cl:14])[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

참가 물질

8

반응물 4

HCID 634876Binap, (A+-)-HCID 27772062-Chloro-6-phenoxybenzylamineHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

생성물 1

HCID 249459814-Chloro-6-(2-chloro-6-phenoxy-benzylamino)-2H-phthalazin-1-one

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2-chloro-6-phenoxy-benzylamine (150 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 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-chloro-6-phenoxy-benzylamino)-2H-phthalazin-1-one: 39 mg (16.3%): m/z (M+H)=412. 1H-NMR (DMSO-d6) δ: 12.34 (s, 1H), 7.90 (d, 1H), 7.35 (m, 5H), 7.21 (dd, 1H), 7.15 (m, 1H), 7.02 (m, 2H), 6.95 (d, 1H), 6.84 (dd, 1H), 4.50 (d, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-b21b5a2bd13a43ae9f3fbfd22e681839
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044041B2

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