Potassium Carbonate → 2-(4-Ethyloxycarbonyl-butylsulfanyl)-5-fluoro-benzoimidazole

HRID 2389504

反応式

HRID 2389504 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([SH:9])=[N:8][C:4]=2[CH:3]=1.[CH2:12]([O:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19]Br)[CH3:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:14][C:15]([CH2:16][CH2:17][CH2:18][CH2:19][S:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[N:6]=1)=[O:21])[CH3:13]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 178505474HCID 178505474、化合物

生成物 1

HCID 693141242-(4-Ethyloxycarbonyl-butylsulfanyl)-5-fluoro-benzoimidazole収率 71.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A suspension of 5-fluoro-1H-benzoimidazole-2-thiol (168 mg, 1 mmol), 5-bromo-pentanoic acid ethyl ester (188 mg, 0.9 mmol, 145 μl) and K2CO3 (276 mg, 2 mmol) in acetone (2 ml) is refluxed for 3 h. It is cooled down and filtered over a short plug of silica gel and rinsed with AcOEt. The solvent is removed in vacuo. The crude is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:2), yielding the title compound (190 mg) in 64% as a brown oil: tR=1.87 min (LC-2), ESI-MS (pos.): m/z 297.28 [M+H]+, ESI-MS (neg.): m/z 295.30 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.25 (t, 3H, CH3), 1.79 (br. t, 4H), 2.36 (br. t, 2H, CH2CO), 3.28 (br. t, 2H, SCH2), 4.14 (q, 2H, CH2O), 6.93 (dt, 1Harom), 7.20 (dd, 1Harom), 7.41 (dd, 1Harom).

後処理

  1. temperatureis refluxed for 3 h
  2. temperatureIt is cooled down
  3. filtrationfiltered over a short plug of silica gel
  4. washrinsed with AcOEt
  5. customThe solvent is removed in vacuo
  6. customThe crude is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:2)

出典と根拠

ORDレコード
ord-2e4f881c10724893bebfe0884f585b57
出典データセット
uspto-grants-2012_09
特許番号
US08273740B2

関連ノート

読み込み中…