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

HRID 1431706Notes

Reaction equation

HRID 1431706 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

The Stille coupled product was prepared according to Procedure E 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 in toluene (10 mL) and heating at reflux for 14 h. 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. 1H NMR (400 MHz, CDCl3) δ ppm 9.14 (1H, dd, J=4.3, 2.0 Hz), 8.72 (1H, ddd, J=4.9, 1.8, 1.0 Hz), 8.65 (1H, dd, J=8.3, 1.9 Hz), 8.09 (1H, dt, J=8.0, 1.1 Hz), 7.90 (1H, td, J=7.7, 1.8 Hz), 7.60 (1H, dd, J=8.3, 4.2 Hz), 7.40 (1H, ddd, J=7.6, 4.8, 1.3 Hz), 2.75 (3H, s)

Workup

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

Sources & evidence

ORD record
ord-743fda19ca1348db856aaaba8ef4611c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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