Water → toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

HRID 2240028ノート

反応式

HRID 2240028 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([S:19]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH2:32][CH2:33][O:34][S:35]([C:38]4[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=4)(=[O:37])=[O:36])[CH:29]=3)[NH:24][N:23]=2)(=[O:21])=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)=O>[CH2:1]([N:24]1[C:25]2[C:30](=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][S:35]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)(=[O:37])=[O:36])=[CH:27][CH:26]=2)[C:22]([S:19]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)(=[O:20])=[O:21])=[N:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 178427773HCID 178427773、化合物

生成物 1

HCID 58812069toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Benzyl bromide (0.46 mL, 3.9 mmol) was added to a stirring suspension of toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (1.85 g, 3.54 mmol) and cesium carbonate (1.28 g, 3.93 mmol) in acetone (60 mL). The reaction mixture was stirred under nitrogen at ambient temperature for 1.5 hours. It was then poured into excess water and extracted with chloroform. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography with 40-50% ethyl acetate in hexane. Drying at 80° C. in vacuo for 30 minutes yielded toluene-4-sulfonic acid 2-[1-benzyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester as a light buff foam (1.39 g, 64.1%); Mass Spectrum (+EI, [M+H]+) m/z 613. 1HNMR (500 MHz, DMSO-d6): δ8.74-8.77 (m, 1H), 8.55-8.57 (m, 1H), 8.25-8.27 (m, 1H), 8.01-8.05 (m, 1H), 7.64-7.76 (m, 4H), 7.58-7.64 (m, 2H), 7.25 (d, 2H, J=7.93 Hz), 7.10-7.19 (m, 5H), 7.07 (d, 1H, J=2.19 Hz), 6.94-6.97 (m, 1H), 5.69 (s, 2H), 4.30-4.32 (m, 2H), 4.14-4.16 (m, 2H), 2.18 ppm (s, 3H). Elemental Analysis for C33H28N2O6S2.0.60 mol H2O: Calcd: C, 63.57; H, 4.72; N, 4.49; Found: C, 63.17; H, 4.63; N, 4.30.

後処理

  1. extractionextracted with chloroform
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography with 40-50% ethyl acetate in hexane
  7. customDrying at 80° C. in vacuo for 30 minutes

出典と根拠

ORDレコード
ord-941eae56f76e489da194ef52c77a037a
出典データセット
uspto-grants-2010_05
特許番号
US07723329B2

反応ノート

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