1,3-Dibromopropane → Methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616141ノート

反応式

HRID 1616141 の反応式
[H-].[Na+].[O:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6][NH:5]1.[Br:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C>[Br:18][CH2:19][CH2:20][CH2:21][N:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[C:4]1=[O:3]

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 60075037Methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate

生成物 1

HCID 67282659Methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate収率 144.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred suspension of sodium hydride (60% in mineral oil, 0.30 g, 7.4 mmol) in DMF (15 mL) under an atmosphere of nitrogen cooled to 0° C. was added methyl 1-oxo-1,2-dihydroisoquinoline-7-carboxylate (1.0 g, 4.9 mmol) in DMF (15 mL) dropwise. The mixture was stirred for 30 mins, then 1,3-dibromopropane (80 μL, 1.28 mmol) was added quickly and the resulting solution was stirred overnight warming to rt slowly. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 30% EtOAc/hexanes) to afford methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.60 g, 38%). LC-MS: (FA) ES+ 326.

後処理

  1. stirringthe resulting solution was stirred overnight
  2. temperaturewarming to rt slowly
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic phases were then washed with water, and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash silica gel chromatography (0% to 30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-cd0eb1e505f648fca52175b017d7016f
出典データセット
uspto-grants-2014_07
特許番号
US08765773B2

反応ノート

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