N-bromobutanimide → 3-bromo-1H-indole-5-sulfonamide

HRID 528844노트

반응식

HRID 528844 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C.OS([O-])=O.[Na+].CCOC(C)=O>[Br:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([S:10]([NH2:13])(=[O:11])=[O:12])[CH:5]=2)[NH:1][CH:2]=1

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 216831001H-Indole-5-sulfonamide2회

생성물 1

HCID 710624653-bromo-1H-indole-5-sulfonamide수율 64.1%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 23665763Sodium Bisulfite용매

실험 절차

To a solution of 1H-indole-5-sulfonamide (Intermediate 54, 100 mg, 0.51 mmol) in DMF (2.0 mL) was added N-bromosuccinimide (91 mg, 0.51 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 30 min and then diluted with sat. aq. NaHSO3 solution and EtOAc. The organic layer was washed with sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using preparative HPLC to give the title compound (90 mg, 61%) as a white solid after lyophilization. 1H NMR (DMSO-d6) δ 11.88 (br s, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.75 (d, J=2.6 Hz, 1H), 7.65-7.63 (m, 1H), 7.59-7.57 (m, 1H), 7.21 (s, 2H); MS (ESI+) m/z 277.1 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with sat. aq. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-4efca17a3b5547229b59fd1a626a7eeb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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