Toluene → HCID 21186228, 화합물

HRID 1107465

반응식

HRID 1107465 반응식
Cl[C:2]1[C:7]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:21]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[CH:22]([CH3:24])[CH3:23].[K].C1(C)C=CC=CC=1>O>[CH2:21]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[C:7]([S:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:27][CH:26]=1)[CH:22]([CH3:24])[CH3:23]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 2773472(4-Isobutylphenyl)boronic acidHCID 5462222PotassiumHCID 211862554-Nitrophenyl 2-chloropyridine-3-sulphonate

생성물 1

HCID 21186228HCID 21186228, 화합물수율 55.3%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

Tetrakis(triphenylphosphine)palladium(b) (0.076 g) was added to a deoxygenated mixture of 4-nitrophenyl 2-chloropyridine-3-sulphonate (0.69 g), 4-isobutylphenylboronic acid (0.47 g), potassium fluorsde (0.38 g), toluene (15 ml) and water (2.5 ml) and the mixture was stirred and heated under reflux for 24 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×80 ml). The organic extracts were washed with saturated sodium chloride solution and then combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with dichoromethane/hexane (1:1-1:0 v/v) then dichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane to give 4-nitrophenyl 2-(4-isobutylphenyl)pyridine-3-sulphonate (0.50 g), m.p. 123-124° C.; 1H NMR (d6 -DMSO): 0.9 (d, 6H), 1.9 (m, 1H), 2.55 (d, 2H), 7.2-7.3 (m, 4H), 7.5 (d, 2H), 7.7 (dd, 1H), 8.2 (d, 2H), 8.4 (dd, 1H), 9.0 (dd, 1H); mass spectrum (+ve FAB, NBA/DMSO): 413 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×80 ml)
  4. washThe organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by gradient elution with dichoromethane/hexane (1:1-1:0 v/v)
  8. customdichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-856b1ab55c394ff980a82ece2cbc3085
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060475

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