4-Pyridinemethanamine → 6-Bromo-1-oxo-2-(pyridin-4-ylmethyl)-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

HRID 907280Notes

Reaction equation

HRID 907280 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[C:5]2[C:13]([O:15][CH3:16])=[O:14].[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][CH:18]=1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:24]([CH2:23][C:20]1[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=1)[CH:6]=[C:5]2[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 575518316-Bromo-1-oxo-1H-isochromene-4-carboxylic acid, methyl ester

Product 1

HCID 575517256-Bromo-1-oxo-2-(pyridin-4-ylmethyl)-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Example 37 step ii) (0.78 g) and pyridin-4-ylmethanamine (0.298 g) in methanol (5 mL) was heated at reflux for 24 hours. The reaction was concentrated to dryness and the crude product triturated with acetonitrile before being purified (SiO2, 5% methanol in dichloromethane as eluent) to give the sub-title compound (0.70 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe reaction was concentrated to dryness
  4. customthe crude product triturated with acetonitrile
  5. custombefore being purified (SiO2, 5% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-156a16cd51e84db79690d93971a73dee
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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