Water → 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1696526노트

반응식

HRID 1696526 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[NH:12][CH2:11][CH2:10]2)(=O)=O.[C:20](=[N:33][NH2:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:21]1([C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:33][NH:34][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[NH:12][CH2:11][CH2:10]3)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79304DiphenylmethylidenehydrazineHCID 534141981-Oxo-1,2,3,4-tetrahydroisoquinolin-6-YL trifluoromethanesulfonate

생성물 1

HCID 866116856-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one수율 50%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 1140Toluene용매

실험 절차

To a suspension of 1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate (1.70 g, 5.76 mmol), benzophenone hydrazone (1.36 g, 6.91 mmol), Cs2CO3 (2.81 g, 8.64 mmol) and DPPF (0.048 g, 0.086 mmol) in degassed PhMe (40 mL) was added Pd(OAc)2 (0.013 g, 0.058 mmol) and the resulting mixture was stirred at RT for 30 min and then heated at 90° C. After 16 h, the mixture was cooled to RT, H2O (50 mL) was added and the mixture was extracted with EtOAc (3×50 mL), dried (MgSO4), concentrated and purified via column chromatography to yield 6-(2-(diphenylmethylene)hydrazinyl)-3,4-dihydroisoquinolin-1(2H)-one (980 mg, 50% yield). 1H NMR (400 MHz, acetone-d6): δ 8.69 (brs, 1H), 7.79 (d, J=9.2 Hz, 1H), 7.63-7.54 (m, 5H), 7.37-7.31 (m, 5H), 7.11-7.08 (m, 2H), 6.67 (brS, 1H), 3.47 (dt, J=7.2, and 3.2 Hz, 2H), 2.90 (t, J=6.6 Hz, 2H); MS (ESI) m/z: 342.0 (M+H+).

후처리

  1. temperatureheated at 90° C
  2. waitAfter 16 h
  3. temperaturethe mixture was cooled to RT
  4. extractionthe mixture was extracted with EtOAc (3×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-8056c0b9efb54381bae95ca07bb15800
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163756B2

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