Benzenesulfonyl chloride → HCID 49758931, 화합물

HRID 1020906노트

반응식

HRID 1020906 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][N:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][N:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 49758931HCID 49758931, 화합물수율 73.9%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

To a mixture of 4-methoxy-7-azaindole (6.4 g, 43.2 mmol) in dichloromethane (200 mL) and 50% aqueous sodium hydroxide (200 mL) was added benzenesulfonyl chloride (6.1 mL, 47.5 mmol) and tetrabutylammonium bromide (1.4 g, 4.3 mmol). The mixture was stirred vigorously at room temperature for 18 hours. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was recrystallized from ethyl acetate and hexanes to give 9.2 g of 1-benzenesulfonyl-4-methoxy-7-azaindole as a yellow solid. 1H NMR (DMSO-d6) δ 8.30 (d, J=5 Hz, 1H), 8.18 (d, 1 Hz, 1H), 7.58 (m, 2H), 7.47 (m, 2H), 6.67 (d, 4 Hz, 1H), 6.61 (d, 4 Hz, 1H), 3.94 (s, 3H). MS (m/z) 289 (M+H).

후처리

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-5038c587efa045b88c5723d41efc326f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716493B2

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