Sodium Carbonate → 2-(5-Chloro-2-fluoro-phenyl)-4-(5-phenyl-pyridin-3-yl)-[1,8]naphthyridine

HRID 1404310Notes

Reaction equation

HRID 1404310 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]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH:3]=1.[C:20]1([C:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[N:30][CH:31]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C:4]2[CH:3]=[C:2]([C:28]3[CH:29]=[N:30][CH:31]=[C:26]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:27]=3)[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 45790037(5-Phenylpyridin-3-yl)boronic acidHCID 53344724HCID 53344724, compound

Product 1

HCID 673633992-(5-Chloro-2-fluoro-phenyl)-4-(5-phenyl-pyridin-3-yl)-[1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

150 mg 4-chloronaphthyridine from example 1, 184 mg 5-phenyl-3-pyridyl boronic acid, 326 mg sodium carbonate and 60 mg tetrakistriphenylphosphine palladium(0) were dissolved with 15 ml dioxan, flushed with nitrogen, and heated to 90° C. After addition of 2 ml water, heating continued at 90° C. for 90 minutes to give a dark turbid solution. Work-up as in example 20 yielded after precipitation with ether 141 mg product with correct LC mass: M+H+ 412 and Rt˜2.53 min.

Workup

  1. customflushed with nitrogen
  2. additionAfter addition of 2 ml water
  3. temperatureheating
  4. customto give a dark turbid solution
  5. customyielded
  6. customafter precipitation with ether 141 mg product with correct LC mass

Sources & evidence

ORD record
ord-becc752b001b42988fcecc545a41102f
Source dataset
uspto-grants-2014_12
Patent number
US08912216B2

Reaction notes

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