Chlorosuccinimide → HCID 71295631, 화합물

HRID 1776873노트

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HRID 1776873 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.C1C(=O)N([Cl:25])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[Cl:25])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 13163448HCID 13163448, 화합물

생성물 1

HCID 71295631HCID 71295631, 화합물수율 98.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-bromo-2-(1H-indol-2-yl)phenol (100 mg, 0.35 mmol) in DMF (1 mL) was added NCS (46 mg, 0.35 mmol), it was allowed to stir at room temperature until LCMS showed the starting material was consumed completely. The reaction solution was extracted with EtOAc, and the combined organic layers were washed with H2O (3×10 mL), brine and dried over Na2SO4. The solvent was removed and the crude product was purified using prep-TLC to provide the desired product of 4-bromo-2-(3-chloro-1H-indol-2-yl)phenol (110 mg, yield: 98.2%). 1H-NMR (CDCl3, 400 MHz) δ 9.25 (s, 1H), 7.80 (d, J=2.4 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.40˜7.43 (m, 1H), 7.20˜7.30 (m, 2H), 7.12 (t, J=4.0 Hz, 1H), 6.86 (t, J=6.0 Hz, 1H), 5.93 (s, 1H). MS (M+H)+: 322/324.

후처리

  1. customwas consumed completely
  2. extractionThe reaction solution was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O (3×10 mL), brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe crude product was purified

출처 및 근거

ORD 기록
ord-32e2cbe0915c4d8190642fe08454f854
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265773B2

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