Benzenemethanamine, 3,5-dichloro- → 4-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one

HRID 1803556

반응식

HRID 1803556 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:16]=[C:17]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:18][NH2:19].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:19][CH2:18][C:17]3[CH:16]=[C:15]([Cl:14])[CH:22]=[C:21]([Cl:23])[CH:20]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

참가 물질

8

반응물 4

HCID 457602Benzenemethanamine, 3,5-dichloro-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

생성물 1

HCID 249485344-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one수율 2.3%

시약·촉매·용매 3

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

실험 절차

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (97 mg, 0.374 mmol), 3,5-dichlorobenzylamine (0.057 mL, 0.424 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), rac-BINAP (70 mg, 0.112 mmol) and NaOtBu (104 mg, 1.08 mmol) in DMA (5 mL) was heated at 80° C. for 1.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one (3 mg) as a white solid, 1H (400 MHz, CDCl3) δ: 4.40 (s, 2H), 6.84 (m, 1H), 6.99 (m, 1H), 7.22 (m, 3H), 8.14 (m, 1H), 10.80 (s, 1H) ppm; m/z (M+1) 353.83.

후처리

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

출처 및 근거

ORD 기록
ord-e5414037facb43e5aecd795d788d6366
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349836B2

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