Iodoethane → HCID 58266581、化合物

HRID 1505948ノート

反応式

HRID 1505948 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:14](I)[CH3:15].[BH4-].[Na+]>CN(C=O)C.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH:12]=[CH:11][CH2:10][N:9]2[CH2:14][CH3:15])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 6340IodoethaneHCID 15152372-(4-Bromophenyl)pyridineHCID 4311764Sodium borohydride

生成物 1

HCID 58266581HCID 58266581、化合物収率 29.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-(4-bromophenyl)pyridine (2.7 g, 11.5 mmol) in DMF (50 mL) was added ethyl iodide (1.9 mL, 23.1 mmol) and the reaction mixture was heated to 80° C. for 16 h. The mixture was cooled then evaporated and the resultant residue dissolved in methanol (100 mL) before addition of sodium borohydride (1.5 g, 39.2 mmol) portionwise. The reaction mixture was stirred at ambient temperature for 1 h then evaporated and saturated aqueous sodium carbonate solution was added. The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated then the residue was purified by flash chromatography (silica, Biotage 100 g column, 50% ethyl acetate in cyclohexane) to afford the title compound (0.9 g, 29%), which was used without further purification. 1H NMR (CDCl3, 300 MHz): 7.47-7.42 (m, 2H), 7.24-7.19 (m, 2H), 5.86-5.74 (m, 2H), 3.47-3.35 (m, 2H), 2.98-2.87 (m, 1H), 2.64-2.46 (m, 1H), 2.33-2.26 (m, 2H), 2.13-2.00 (m, 1H), 0.99 (t, J=7.2 Hz, 3H).

後処理

  1. temperatureThe mixture was cooled
  2. customthen evaporated
  3. customthen evaporated
  4. additionsaturated aqueous sodium carbonate solution was added
  5. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue was purified by flash chromatography (silica, Biotage 100 g column, 50% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-154a9954203d41e8b436e5a0adff5404
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

読み込み中…