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

HRID 1667438

반응식

HRID 1667438 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.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23].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:23][CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:16]3[S:15][CH:19]=[CH:18][CH:17]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

참가 물질

8

반응물 4

HCID 634876Binap, (A+-)-HCID 185257241-(2-Thien-2-ylphenyl)methanamine hydrochlorideHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

생성물 1

HCID 249463444-Chloro-6-(2-thiophen-2-yl-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-thiophen-2-yl-benzylamine hydrochloride (145 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (108 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-thiophen-2-yl-benzylamino)-2H-phthalazin-1-one: 65 mg (30.5%): m/z (M+H)=368. 1H-NMR (DMSO-d6) δ: 12.34 (s, 1H), 7.91 (d, 1H), 7.64 (m, 2H), 7.47 (m, 2H), 7.37 (m, 2H), 7.25 (dd, 1H), 7.16 (m, 1H), 7.11 (m, 1H), 6.64 (s, 1H), 4.43 (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-d71d56eed8874d4a8c8e32679a33ca2c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044041B2

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