Sodium Carbonate → 3-[1-Benzenesulfonyl-3-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester

HRID 1394617ノート

反応式

HRID 1394617 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]=[C:10]2I)[CH3:6].[CH2:27]([O:31][C:32]1[C:37]([CH:38]([CH3:40])[CH3:39])=[CH:36][C:35]([CH:41]([CH3:43])[CH3:42])=[CH:34][C:33]=1B(O)O)[CH2:28][CH2:29][CH3:30].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCCCCC.O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]=[C:10]2[C:33]1[CH:34]=[C:35]([CH:41]([CH3:43])[CH3:42])[CH:36]=[C:37]([CH:38]([CH3:39])[CH3:40])[C:32]=1[O:31][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:6]

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 692188963-(1-Benzenesulfonyl-3-iodo-1H-indol-5-yl)-but-2-enoic acid methyl ester

生成物 1

HCID 692206043-[1-Benzenesulfonyl-3-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester収率 151.2%

試薬・触媒・溶媒 5

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

3-(1-Benzenesulfonyl-3-iodo-1H-indol-5-yl)-but-2-enoic acid methyl ester (653 mg, 1.35 mmol) and (2-butoxy-3,5-diisopropylphenyl)-boronic acid (415 mg, 1.49 mmol) were dissolved in toluene (8 mL) under a nitrogen atmosphere. Tetrakis(triphenylphosphine) palladium (172 mg, 0.15 mmol) and 2N Na2CO3 (2.7 mL) was added and the biphasic mixture stirred at 80° C. for 6 h. The reaction was judged complete by TLC (9:1) in hexane:ethyl acetate but was allowed to stir overnight at room temperature. The reaction was diluted with water (5 mL)/ethyl acetate (15 mL). The layers were separated and the aqueous washed with ethyl acetate (10 mL). The organic portions were passed through a pad of Celite, dried (MgSO4), filtered and concentrated in vacuo to provide 1.20 g of a dark brown oil. Chromatography (SiO2, hexanes/ethyl acetate) provided 294 mg (37%) of a yellow foam. 1H NMR (250 MHz, CDCl3): δ 8.06 (d, 1H, J=8.7), 7.94 (m, 2H), 7.80 (s, 1H), 7.75 (d, 1H, J=1.7), 7.56-7.45 (m, 4H), 7.13 (m, 2H), 6.14 (d, 1H, J=1.2), 3.75 (s, 3H), 3.39 (sep, 1H, J=6.9), 3.29 (t, 2H, J=6.3), 2.93 (sep, 1H, J=6.9), 2.60 (d, 3H, J=1.2), 1.29 (d, 7H, J=6.9), 1.27 (d, 7H, J=6.9), 1.22 (m, 2H), 0.62 (t, 3H, J=7.2). MS [EI+] 588 (M+H)+.

後処理

  1. stirringto stir overnight at room temperature
  2. customThe layers were separated
  3. washthe aqueous washed with ethyl acetate (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-52fa6a63d4154c339d010de42da5724d
出典データセット
uspto-grants-2008_03
特許番号
US07348359B2

反応ノート

読み込み中…