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

HRID 1751098노트

반응식

HRID 1751098 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b93f4da3f7424b9aba75d43a96a08e44
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156840B2

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