N-bromobutanimide → (3-Bromomethyl-6-chloro-isoquinolin-5-yl)-acetic acid methyl ester

HRID 505214Notes

Reaction equation

HRID 505214 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH3:16])[N:9]=[CH:10]2.[Br:18]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16][Br:18])[N:9]=[CH:10]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66882229(6-Chloro-3-methyl-isoquinolin-5-yl)-acetic acid methyl ester

Product 1

HCID 66880745(3-Bromomethyl-6-chloro-isoquinolin-5-yl)-acetic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (6-Chloro-3-methyl-isoquinolin-5-yl)-acetic acid methyl ester (1.9 g, 7.63 mmol) in tetrachloromethane (190 mL) was added N-bromosuccinimide (1.36 g, 7.63 mmol). The reaction mixture was heated to 40° C. for 1 h under simultaneous irradiation by a 300 W UV lamp, filtered and the filtrate concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, cyclohexane/EtOAc 80:20) to afford the title compound as a white powder (1.00 g, 3.05 mmol, 40%). MS (ES+): 328 (M(C13H1179Br35ClNO2)+H)+.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe crude product was purified by flash column chromatography (silica gel, cyclohexane/EtOAc 80:20)

Sources & evidence

ORD record
ord-58ac8ee9878147209e816f01ae019126
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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