Hydrochloric Acid → Ethyl 5-bromo-2-(cyclopent-1-en-1-yl)-6-(methylsulfonamido)benzofuran-3-carboxylate

HRID 595581ノート

反応式

HRID 595581 の反応式
[NH2:1][C:2]1[C:20]([Br:21])=[CH:19][C:5]2[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([C:9]3[CH2:13][CH2:12][CH2:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[Br:21][C:20]1[C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][C:4]2[O:8][C:7]([C:9]3[CH2:13][CH2:12][CH2:11][CH:10]=3)=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 90332430Ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylate

生成物 1

HCID 90332449Ethyl 5-bromo-2-(cyclopent-1-en-1-yl)-6-(methylsulfonamido)benzofuran-3-carboxylate収率 96.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylate (3.63 g, 10.37 mmol) and pyridine (2.46 g, 31.1 mmol) in DCM (30 mL) was added dropwise methanesulfonyl chloride (2.37 g, 20.7 mmol) at 0° C., then the mixture was stirred at 25° C. overnight. 10% HCl(a.q.) was added, then the mixture was extracted with DCM (50 mL*3), dried over Na2SO4, and concentrated to give the product of ethyl 5-bromo-2-(cyclopent-1-en-1-yl)-6-(methylsulfonamido)benzofuran-3-carboxylate (4.3 g, yield: 96%). 1H-NMR (CDCl3, 400 MHz) δ 8.19 (s, 1H), 7.80 (s, 1H), 7.22 (t, J=2.0 Hz, 1H), 6.84 (s, 1H), 4.45 (q, J=7.2 Hz, 2H), 2.99 (s, 3H), 2.89˜2.94 (m, 2H), 2.62˜2.67 (m, 2H), 2.06 (t, J=7.6 Hz, 2H), 1.47 (t, J=7.2 Hz, 3H). MS (M+H)+: 428/430.

後処理

  1. extractionthe mixture was extracted with DCM (50 mL*3)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-05195766ce534f80a381c64d1234f5ca
出典データセット
uspto-grants-2016_01
特許番号
US09242998B2

反応ノート

読み込み中…