Water → 5-Chloro-1-(phenylsulfonyl)-4-azaindole

HRID 628446노트

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HRID 628446 반응식
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][N:10]([S:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:19])=[O:18])[C:5]2=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 123842375-Chloro-1H-pyrrolo(3,2-b)pyridine

생성물 1

HCID 181764365-Chloro-1-(phenylsulfonyl)-4-azaindole

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 5-chloro-1H-pyrrolo[3,2-b]pyridine (20. g, 130 mmol, Adesis) in DCM (200 mL) was added benzenesulfonyl chloride (20. mL, 160 mmol, Aldrich), triethylamine (27 mL, 200 mmol) and 4-dimethylaminopyridine (0.80 g, 6.6 mmol, Aldrich). The reaction mixture was stirred overnight. Water was added and the mixture was stirred for 4 h. Layers were separated and the organic phase was washed sequentially with 1 N HCl, water, saturated solution of NaHCO3, and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to give an orange solid, which was triturated with MeOH (100 mL). The solid was filtered, washed with MeOH, and dried at 40° C. under high vacuum overnight. Additional product was obtained by flash chromatography of the filtrate (eluting with a gradient from 0-60% EtOAc in hexanes). Yield: (26.8 g, 95%).

후처리

  1. stirringthe mixture was stirred for 4 h
  2. customLayers were separated
  3. washthe organic phase was washed sequentially with 1 N HCl, water, saturated solution of NaHCO3, and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange solid, which
  8. customwas triturated with MeOH (100 mL)
  9. filtrationThe solid was filtered
  10. washwashed with MeOH
  11. customdried at 40° C. under high vacuum overnight
  12. customAdditional product was obtained by flash chromatography of the filtrate (
  13. washeluting with a gradient from 0-60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-2db88590cbe1440a9bbad5e59e4ceca0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309246B2

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