Triethylamine → 3-(2-Oxoindolin-3-yl)propyl methanesulfonate

HRID 2363029ノート

反応式

HRID 2363029 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 122442773-(3-Hydroxypropyl)indolin-2-one

生成物 1

HCID 580466483-(2-Oxoindolin-3-yl)propyl methanesulfonate収率 99.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methanesulfonyl chloride (0.42 mL, 5.39 mmol) was added dropwise at 0° C. to 3-(3-hydroxypropyl)indolin-2-one (1.03 g, 5.39 mmol) and triethylamine (1.13 mL, 8.09 mmol) in dichloromethane (20 mL). The mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction was washed with 2M aqueous hydrochloric acid and brine, dried (MgSO4), and evaporated. The residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes) to give product as an oil (1.45 g, quant.); 1H NMR (DMSO-d6); δ1.66-1.70 (m, 2H); 1.85-1.94 (m, 2H); 3.15 (s, 3H); 3.48 (t, J=6.4 Hz, 1H); 4.19 (t, J=6.4 Hz, 2H); 6.82 (d, J=8 Hz, 1H); 6.96 (m, 1H); 7.18 (m, 1H); 7.25 (d, J=7.6 Hz, 1H); 10.4 (s, 1H); MS for C12H15NO4S m/z 270 (M+H)+.

後処理

  1. washThe reaction was washed with 2M aqueous hydrochloric acid and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by Biotage flash column chromatography (30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-9ab55b67724747f3b789a22abd3af351
出典データセット
uspto-grants-2014_04
特許番号
US08691836B2

反応ノート

読み込み中…