2-Methyl-6-(tributylstannyl)pyridine → HCID 53344726, compound

HRID 1914936Notes

Reaction equation

HRID 1914936 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][C:14]1[N:19]=[C:18]([Sn](CCCC)(CCCC)CCCC)[CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:12][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:13])[N:19]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 114631832-Methyl-6-(tributylstannyl)pyridineHCID 184493022,4-Dichloro-1,8-naphthyridine

Product 1

HCID 53344726HCID 53344726, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.69 g (8.47 mmol) 2,4-dichloro-[1,8]naphthyridine and 3.24 g (8.47 mmol) 6-methyl-2-(tributylstannyl)-pyridine in 8.5 ml toluene under nitrogen was heated to 80° C. Then 178 mg (0.254 mmol) bis-(triphenylphosphine)-palladium(II)-chloride were added. The mixture was stirred for 16 hrs at 80° C. and then cooled to 0° C. in an ice bath. The precipitate was filtered off, washed with ice cold toluene and petrolether and dried in vacuum. This yielded 4-chloro-2-(6-methylpyridin-2-yl)-[18]naphthyridine as gray felted needles; HPLC-MS: 2.25 min, [M+H] 256.

Workup

  1. temperaturecooled to 0° C. in an ice bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with ice cold toluene and petrolether
  4. customdried in vacuum
  5. custom2.25 min, [M+H] 256

Sources & evidence

ORD record
ord-a0052edba4ff46a4abbb4052dd891efb
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

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