2-(Tributylstannyl)pyridine → 4-Chloro-3-methyl-2-(pyridin-2-yl)-1,7-naphthyridine

HRID 1618737Notes

Reaction equation

HRID 1618737 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>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](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 596315492,4-Dichloro-3-methyl-1,7-naphthyridine

Product 1

HCID 596313804-Chloro-3-methyl-2-(pyridin-2-yl)-1,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure E using 2,4-dichloro-3-methyl-1,7-naphthyridine (200 mg, 0.94 mmol), 2-tri-n-butylstannylpyridine (0.35 mL, 0.939 mmol), Pd(PPh3)4 (108 mg, 0.094 mmol) with heating in toluene (10 mL) for 14 h. After purification 4-chloro-3-methyl-2-(pyridin-2-yl)-1,7-naphthyridine was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 4-chloro-3-methyl-2-(pyridin-2-yl)-1,7-naphthyridine
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-12c44f499fca41c7a48ea11610d47f27
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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