Phosphorus oxybromide → HCID 20484895, compound

HRID 647437Notes

Reaction equation

HRID 647437 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:8]=[C:9]2O)=[CH:4][CH:3]=1.P(Br)(Br)([Br:31])=O>>[Br:31][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([N:13]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH3:14])[N:8]=1

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178472170HCID 178472170, compound

Product 1

HCID 20484895HCID 20484895, compound

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-{4-[N-(7-chloro-1-hydroxyisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.00 g) and phosphorus oxybromide was heated at 120° C. for 10 mins. The mixture was cooled, poured into ice-water and extracted with dichloromethane, which was dried (MgSO4) and evaporated to give an oil. Purification by column chromatography over silica gel (eluant dichloromethane) gave ethyl 2-{4-[N-(1-bromo-7-chloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.83 g) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane, which
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customto give an oil
  6. customPurification by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-2b810f5e212741eb84e3e9b779816288
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

Loading…