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Hexane → 3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester

HRID 1394624
ノート
印刷プレビュー

反応式

HRID 1394624 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[C:13](Br)[CH:12]=[CH:11][CH:10]=2)[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+].CCCCCC>C1(C)C=CC=CC=1.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.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[C:13]([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])[CH:12]=[CH:11][CH:10]=2)[CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 692210343-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl ester

生成物 1

HCID 692207963-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester収率 48%

試薬・触媒・溶媒

4
HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
75 °C

実験手順

3-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl ester (117 mg, 0.27 mmol) and 2-butoxy-3,5-diisopropylphenyl-boronic acid (150 mg, 54 mmol) (see Example 17, step B) were dissolved in toluene (2 mL) under a nitrogen atmosphere. Tetrakis(triphenylphosphine) palladium (31 mg, 0.027 mmol) and 2N Na2CO3 (0.7 mL) were added and the biphasic mixture stirred at 75° C. for 16 h. The reaction was diluted with water/ethyl acetate. The layers were separated and the aqueous layer was washed with ethyl acetate. The organic portions were passed through a pad of Celite, dried (MgSO4), filtered and concentrated in vacuo to provide 243 mg of a crude black oil. Radial chromatography using (99:1) hexane:ethyl acetate provided 76 mg (48%) of product. 1H NMR (250 MHz, CDCl3): δ 8.15 (d, 1H, 8.2), 7.66 (m, 2H), 7.46-7.27 (m, 5H), 7.11 (d, 1H, J=2.2), 6.90 (d, 1H, J=2.2), 6.54 (s, 1H), 6.05 (d, 1H, J=1.2), 3.80 (s, 3H), 3.36 (sep, 1H, J=6.9), 3.04 (t, 2H, J=6.0), 2.88 (sep, 1H, J=6.9), 2.61 (d, 3H, J=1.2), 1.25 (d, 6H, J=6.9), 1.24 (d, 6H, J=6.9), 1.08-0.87 (m, 4H), 0.62 (t, 3H, J=7.0). MS [EI+] 588 (M+H)+ [EI−] 586 (M−H)+.

後処理

  1. customThe layers were separated
  2. washthe aqueous layer was washed with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide 243 mg of a crude black oil

出典と根拠

ORDレコード
ord-c440ffa8c5b648f88785f773496bbb4f
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07348359B2

反応ノート

読み込み中…

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