Citric Acid → Tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate

HRID 454775노트

반응식

HRID 454775 반응식
[C:1]1(OB=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:27][C:28]2[CH:40]=[C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:38]=[CH:37][C:29]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:26])[CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:41]1([C:39]2[CH:38]=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:28]([NH:27][C:25]([C:21]3[CH:20]=[C:19]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:24]=[CH:23][N:22]=3)=[O:26])[CH:40]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

9

반응물 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, Tribasic2회HCID 14438906HCID 14438906, 화합물2회HCID 58508497Tert-butyl 2-(4-chloropyridine-2-carboxamido)-4-phenylbenzoate

생성물 1

HCID 58508724Tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate수율 98.3%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매2회HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매2회HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Phenylboranic acid (21 mg), tripotassium phosphate (69 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added to a toluene (1.2 mL) solution of tert-butyl 2-(4-chloropyridine-2-carboxamido)-4-phenylbenzoate (60 mg), followed by heating to reflux under a nitrogen atmosphere for 3 hours. The reaction mixture was cooled to room temperature, and then phenylboranic acid (5.4 mg), tripotassium phosphate (16 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.2 mg), and palladium(II) acetate (1.3 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and a 10% aqueous solution of citric acid were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate] to obtain 65 mg of tert-butyl 4-phenyl-2-(4-phenylpyridine-2-carboxamido)benzoate as a colorless oily substance.

후처리

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 3 hours
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-85% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-bdee635596ce46458cb31fce7ad13748
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492582B2

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