Toluene → HCID 21186228、化合物

HRID 1107465

反応式

HRID 1107465 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 21186228HCID 21186228、化合物収率 55.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-856b1ab55c394ff980a82ece2cbc3085
出典データセット
uspto-grants-2000_05
特許番号
US06060475

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