Chlorosuccinimide → HCID 71295631、化合物

HRID 1776873ノート

反応式

HRID 1776873 の反応式
[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

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 13163448HCID 13163448、化合物

生成物 1

HCID 71295631HCID 71295631、化合物収率 98.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-32e2cbe0915c4d8190642fe08454f854
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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