2-(Tributylstannyl)pyridine → 4-Chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine

HRID 1618731Notes

Reaction equation

HRID 1618731 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCCC[Sn]([C:27]1[N:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(CCCC)CCCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:13][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][N:32]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 220826612,4-Dichloro-3-methyl-1,8-naphthyridine

Product 1

HCID 596310684-Chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure E by using 2,4-dichloro-3-methyl-1,8-naphthyridine (540 mg, 2.53 mmol), 2-(1,1,1-tributylstannyl)pyridine (933 μL, 2.53 mmol), Pd(PPh3)4 (293 mg, 0.253 mmol) in toluene (10 mL) at reflux for 14 h. After this time the reaction was allowed to cool to rt and evaporated in vacuo. The resulting residue was triturated with hexanes and the solid was dried under vacuum to give 4-chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine.

Workup

  1. customPrepared
  2. temperatureat reflux for 14 h
  3. customevaporated in vacuo
  4. customThe resulting residue was triturated with hexanes
  5. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-61fdef812ed3461e8c07e11d1fab6435
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…