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

HRID 1696526ノート

反応式

HRID 1696526 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 1140Toluene溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-8056c0b9efb54381bae95ca07bb15800
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

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