Water → N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-(2-pyridyl)phenyl)pyridine-3-sulphonamide

HRID 1107489ノート

反応式

HRID 1107489 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Sn](CCCC)(CCCC)CCCC.[CH2:20]([O:24][C:25]([N:27]([C:44]1[C:49]([O:50][CH3:51])=[N:48][C:47]([CH3:52])=[CH:46][N:45]=1)[S:28]([C:31]1[C:32]([C:37]2[CH:42]=[CH:41][C:40](I)=[CH:39][CH:38]=2)=[N:33][CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])=[O:26])[CH:21]([CH3:23])[CH3:22].O>C1(C)C(C)=CC=CC=1.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>[CH2:20]([O:24][C:25]([N:27]([C:44]1[C:49]([O:50][CH3:51])=[N:48][C:47]([CH3:52])=[CH:46][N:45]=1)[S:28]([C:31]1[C:32]([C:37]2[CH:42]=[CH:41][C:40]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:39][CH:38]=2)=[N:33][CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])=[O:26])[CH:21]([CH3:23])[CH3:22]

参加物

6

反応物 3

HCID 962WaterHCID 6077842-(Tributylstannyl)pyridineHCID 211862652-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

生成物 1

HCID 21186311N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-(2-pyridyl)phenyl)pyridine-3-sulphonamide収率 31.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 7237O-Xylene溶媒

反応条件

温度
125 °C

実験手順

Tetrakis(triphenylphosphine)palladium (0) (45 mg) was added to a deoxygenated solution of (2-pyridyl)tributylstannane (294 mg) and N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-iodophenyl)pyridine-3-sulphonamide(465 mg) in xylene (15 ml). The mixture was stirred and heated under argon at 125° C. for 17 hours and then allowed to cool to ambient temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column, eluting with 0-65% ethyl acetate/hexane to give N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-(2-pyridyl)phenyl)pyridine-3-sulphonamide (135 mg) as a foam; 1H NMR (CDCl3): 0.7 (d, 6H), 1.7 (m, 1H), 2.5 (s, 3H), 3.8 (d, 2H), 4.0 (s, 3H), 7.5 (dd, 2H), 7.6-7.8 (m, 4H), 7.9 (s, 1H), 8.1 (dd, 2H), 8.7 (dd, 1H), 8.9 (dd, 1H), 9.0 (dd, 1H); mass spectrum (+ve ESP): 534 (M+H)+.

後処理

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialthen dried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  7. washeluting with 0-65% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-7a4552888e994bc89b7035d9f24d2f6f
出典データセット
uspto-grants-2000_05
特許番号
US06060475

反応ノート

読み込み中…