Benzenesulfonyl chloride → 1-Benzenesulfonyl-7-methoxy-1H-indole

HRID 42446

반응식

HRID 42446 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21])[CH:9]=[CH:8]2

참가 물질

5

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 766607-Methoxy-1H-indole

생성물 1

HCID 117788011-Benzenesulfonyl-7-methoxy-1H-indole수율 62.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a cooled (ice water bath) solution of 7-(methyloxy)-1H-indole (3 g, 20.38 mmol) in DMF (100 mL) was added sodium hydride (0.618 g, 24.46 mmol) portionwise. After 15 minutes a solution of benzenesulfonyl chloride (3.94 mL, 30.6 mmol) in 20 ml of DMF was added dropwise. The reaction mixture was stirred at RT for 24 h, at which time it was concentrated. The residue was dissolved in DCM (100 ml) and washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography (Biotage; 0% to 100% DCM:Hex; 50 g-HP-silica gel column) to give 3.65 g of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.65 (s, 3H), 6.60-6.75 (m, 2H), 7.08-7.22 (m, 2H), 7.40-7.62 (m, 3H), 7.77-7.92 (m, 3H). MS (ES) [M+H]+ 288.0.

후처리

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in DCM (100 ml)
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (Biotage; 0% to 100% DCM:Hex; 50 g-HP-silica gel column)

출처 및 근거

ORD 기록
ord-3330f67c2d1f402b88d3b9a934e454b1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536179B2

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