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

HRID 628446ノート

反応式

HRID 628446 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2db88590cbe1440a9bbad5e59e4ceca0
出典データセット
uspto-grants-2016_04
特許番号
US09309246B2

反応ノート

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