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

HRID 1620241노트

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HRID 1620241 반응식
[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]

참가 물질

6

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 681821876,7-Dimethoxy-1-methylisoquinolin-3-yl acetate2회

생성물 1

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

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

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온도
130 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c47c5f1928b84db8b6ab7d3b7efe91ca
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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