Benzoyl Peroxide → 1-(Bromomethyl)-6,7-dimethoxyisoquinolin-3-yl acetate

HRID 1620241ノート

反応式

HRID 1620241 の反応式
[C:1]([O:4][C:5]1[N:6]=[C:7]([CH3:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)(=[O:3])[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:45])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:4][C:5]1[N:6]=[C:7]([CH2:19][Br:45])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 681821876,7-Dimethoxy-1-methylisoquinolin-3-yl acetate2 回

生成物 1

HCID 681822701-(Bromomethyl)-6,7-dimethoxyisoquinolin-3-yl acetate収率 41%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

To a solution of 6,7-dimethoxy-1-methylisoquinolin-3-yl acetate SIL 32158 (261 mg, 1.00 mmol) in dry CCl4 (5 mL) in a 10 mL microwave vial equipped with a magnetic stirrer was added benzoyl peroxide (12 mg, 0.05 mmol) followed by NBS (178 mg, 1.00 mmol) and the mixture was stirred for 15 min at 130° C. under microwave irradiation. After cooling to RT, the mixture was diluted with CH2Cl2 (20 mL), washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25) gave 1-(bromomethyl)-6,7-dimethoxyisoquinolin-3-yl acetate SIL 32162 as a yellow solid (140 mg, 41% yield).

後処理

  1. temperatureAfter cooling to RT
  2. washwashed with brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25)

出典と根拠

ORDレコード
ord-c47c5f1928b84db8b6ab7d3b7efe91ca
出典データセット
uspto-grants-2014_07
特許番号
US08772316B2

反応ノート

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