Benzenesulfonyl chloride → HCID 10156873, 화합물

HRID 1766275노트

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HRID 1766275 반응식
C[N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[C:4]([CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:3]1.[H-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:31](OCC)(=O)C>C1COCC1.C(OCC)C>[CH3:31][C:9]1[CH:8]=[C:7]([O:11][S:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])[CH:6]=[C:5]2[C:10]=1[NH:2][CH:3]=[C:4]2[CH:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

참가 물질

7

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 179801241-methyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-ol

생성물 1

HCID 10156873HCID 10156873, 화합물수율 66%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-4 °C

실험 절차

To a suspension of 1-methyl-3-(1-methylpiperdin-4-yl)-5-hydroxy-1H-indole (2.52 mmol, 0.616 g) in THF (6.4 mL) at room temperature was added 60% sodium hydride (3.03 mmol, 0.121 g). After stirring 15 minutes, benzenesulfonyl chloride (2.77 mmol, 0.490 g) was added. Reaction stirred at room temperature for 24 hours. Reaction then treated with ethyl acetate (25 mL) and washed with water (2×25 mL) then brine (25 mL). The organic phase was dried over sodium sulfate, filtered, concentrated in vacuo to afford an oil. The oil was subjected to normal phase radial chromatography, 4 mm plate eluting with 9:1 chloroform:2M ammonia in methanol. Fractions containing product combined, concentrated in vacuo to afford an oil. The oil was dissolved in diethyl ether. The solution was cooled at −4° C. which resulted in crystal formation. Crystals collected by filtration to afford 0.639 g (66%) of the title compound: mp=118° C.; mass spectrum (ion spray): m/z=385 (M); 1H NMR (DMSOd6): 7.85-7.77 (m, 3H), 7.67-7.62 (m, 2H), 7.12 (d, J=2.20 Hz, 1H), 6.69 (d, J=2.20 Hz, 1H), 6.60 (d, J=1.46 Hz, 1H), 2.77-2.68 (bd, 2H), 2.43 (m, 1H), 2.37 (s, 3H), 2.19 (s, 3H), 1.92 (m, 2H), 1.71-1.62 (m, 2H), 1.52 (m, 2H); Calculated for C21H24N2O3S: C, 65.60; H, 6.29; N, 7.29. Found: C, 65.64; H, 6.45; N, 7.19.

후처리

  1. customReaction
  2. stirringstirred at room temperature for 24 hours
  3. customReaction
  4. washwashed with water (2×25 mL)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford an oil
  9. washeluting with 9:1 chloroform
  10. additionFractions containing product
  11. concentrationconcentrated in vacuo
  12. customto afford an oil
  13. customresulted in crystal formation
  14. filtrationCrystals collected by filtration

출처 및 근거

ORD 기록
ord-a9eca62e2ea74dbaa7d293a2832475d3
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230011B2

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