Toluene → 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide

HRID 361426

반응식

HRID 361426 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([N:11]([C:20]1[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=1)[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:10])=[O:9].[CH2:29]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[CH:30]([CH3:32])[CH3:31].C1(C)C=CC=CC=1.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.CCOCC.C(O)C>[CH2:29]([C:33]1[CH:38]=[CH:37][C:36]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[S:8]([N:11]([C:20]2[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=2)[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:10])=[O:9])=[CH:35][CH:34]=1)[CH:30]([CH3:32])[CH3:31]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2773472(4-Isobutylphenyl)boronic acidHCID 21186278HCID 21186278, 화합물

생성물 1

HCID 211862384-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide수율 77.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (0.018 g) was added to a deoxygenated mixture of 4-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2(trimethylsilyl) ethoxymethyl]pyridine-3-sulphonamide (0.225 g), 4-isobutylphenylboronic acid (0.109 g), toluene (4 ml), ethanol (2 ml) and 2M sodium carbonate solution (6 ml) and the mixture was stirred and heated under reflux for 18 hours. Ether (25 ml) was added and the mixture was washed with water (2×25 ml) and saturated sodium chloride solution. Aqueous layers were back-extracted with ether (25 ml). The organic extracts were combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 25-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]-pyridine-3-sulphonamide (0.213 g) as an oil; 1H NMR (d6 -DMSO): -0.1 (s, 9 H), 0.7 (t, 2 H), 0.9 (d, 6 H), 1.9 (m, 1 H), 2.45 (s, 3 H), 2.5 (d, 2 H), 3.5 (t, 2 H), 3.8 (s, 3 H), 4.7 (s, 2 H), 7.2 (d, 2 H), 7.3 (d, 2 H), 7.4 (d, 1 H), 8.0 (s, 1 H), 8.8 (d, 1 H), 9.2 (s, 1 H); mass spectrum (+ve ESP): 543 (M+H)+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. washthe mixture was washed with water (2×25 ml) and saturated sodium chloride solution
  4. extractionAqueous layers were back-extracted with ether (25 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by gradient elution with 25-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column

출처 및 근거

ORD 기록
ord-a975d4131b974a2bac5be506f3fa8f3f
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866568

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