Ethanol → N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

HRID 2287407노트

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HRID 2287407 반응식
[CH2:1]([O:5][C:6]([N:8]([C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([CH3:27])=[CH:21][N:20]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1I)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:1]([O:5][C:6]([N:8]([C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([CH3:27])=[CH:21][N:20]=1)[S:9]([C:12]1[C:13]([C:31]2[CH:32]=[CH:33][C:28]([CH3:34])=[CH:29][CH:30]=2)=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3]

참가 물질

7

반응물 4

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 18704832N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

생성물 1

HCID 18704823N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

A mixture of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (0.252 g) 4-methylbenzeneboronic acid (0.068 g), tetrakis(triphenylphosphine)palladium(0) (0.0115 g), toluene (2.5 ml), ethanol (1.25 ml) and 2H sodium carbonate solution (3.75 ml) was stirred vigorously and heated under reflux for 2 hours under an atmosphere of argon. Water (10 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The combined extracts were washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v), to give N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.182 g); 1H NMR (DMSO-d6): 0.6 (d,6H), 1.55-1.75 (m,1H), 2.35 (s,3H), 2.5 (s,3H), 3.85 (d,2H), 3.95 (s,3H), 7.15-7.25 (m,4H), 7.35-7.45 (m,1H), 7.7-7.8 (m,2H), 8.15 (s,1H), 8.45-8.55 (m,1H); mass spectrum (+ve FAB, methanol/NBA): 470 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hours under an atmosphere of argon
  3. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
  4. washThe combined extracts were washed with saturated sodium chloride solution (25 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:4 v/v)

출처 및 근거

ORD 기록
ord-ffec611185f8450498fab79d18d853b9
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083951

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