Sodium Carbonate → 4-Isoquinolin-4-yl-2-(6-methyl-pyridin-2-yl)-[1,8]naphthyridine

HRID 1914962Notes

Reaction equation

HRID 1914962 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[CH:3]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](B(O)O)=[CH:21][N:20]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)[CH:3]=2)=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 3761204Isoquinoline-4-boronic acidHCID 53344726HCID 53344726, compound

Product 1

HCID 666319524-Isoquinolin-4-yl-2-(6-methyl-pyridin-2-yl)-[1,8]naphthyridineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

190 mg 4-chloro naphthyridine from example 3, 341 mg 4-isoquinoline boronic acid pinacole ester, 473 mg sodium carbonate were dissolved with 20 ml dioxan and 5 ml water, flushed with nitrogen, and 86 mg tetrakistriphenylphosphine palladium(0) were added. After 90 min reflux, workup as in example 20 yielded a grey-brownish oil, which was crystallized with ether to give 176 mg correct product as a brownish powder with correct LC_MS: M+H+ 349 and Rf˜1.76 min.

Workup

  1. customflushed with nitrogen, and 86 mg tetrakistriphenylphosphine palladium(0)
  2. additionwere added
  3. temperatureAfter 90 min reflux
  4. customworkup as in example 20 yielded a grey-brownish oil, which
  5. customwas crystallized with ether

Sources & evidence

ORD record
ord-b9e94e625f69418c89eb43055f194abc
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

Loading…