Toluene → HCID 66990508, 화합물

HRID 454606

반응식

HRID 454606 반응식
[CH3:1][NH:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1.[CH2:25]([O:32][C:33]1[CH:60]=[CH:59][C:58](Br)=[CH:57][C:34]=1[C:35]([NH:37][C:38]1[CH:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:48]=[CH:47][C:39]=1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(Cl)(Cl)Cl.O>[CH2:25]([O:32][C:33]1[CH:60]=[CH:59][C:58]([N:2]([CH3:1])[CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:57][C:34]=1[C:35]([NH:37][C:38]1[CH:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:48]=[CH:47][C:39]=1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

10

반응물 4

HCID 1140TolueneHCID 62657Potassium Phosphate, Tribasic3회HCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amine3회HCID 66990333Tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate

생성물 1

HCID 66990508HCID 66990508, 화합물수율 59.6%

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매3회HCID 9811564Bis(dibenzylideneacetone)palladium촉매3회HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매3회HCID 962Water용매HCID 6212Chloroform용매

실험 절차

N-Methyl-2-(pyrrolidin-1-yl)ethylamine (0.086 g), tripotassium phosphate (0.17 g), tris(dibenzylideneacetone)dipalladium(0) (2.5 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (6.4 mg), and palladium(II) acetate (1.2 mg) were added to a toluene (2.3 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate (0.15 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then N-methyl-2-(pyrrolidin-1-yl)ethylamine (0.017 g), tripotassium phosphate (0.029 g), tris(dibenzylideneacetone)dipalladium(0) (2.5 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (6.4 mg), and palladium(II) acetate (1.2 mg) were added to the reaction mixture, followed by heating to reflux under a nitrogen atmosphere for 7 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then N-methyl-2-(pyrrolidin-1-yl)ethylamine (0.017 g), tripotassium phosphate (0.029 g), tris(dibenzylideneacetone)dipalladium(0) 2.5 mg, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (6.4 mg), and palladium(II) acetate (1.2 mg) were added to the reaction mixture, followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and water and chloroform were added thereto. The insoluble substance was removed by filtration. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.097 g of tert-butyl 2-(2-(benzyloxy)-5-(methyl(2-(pyrrolidin-1-yl)ethyl)amino)benzamido)-4-phenylbenzoate.

후처리

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 7 hours and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. temperatureby heating
  7. temperatureto reflux under a nitrogen atmosphere for 3 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. customThe insoluble substance was removed by filtration
  10. customThe organic layer was separated
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

출처 및 근거

ORD 기록
ord-2946131bcfc44099b0ec69157b34f300
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492582B2

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