4-Methyl-2-(tributylstannyl)pyridine → 4-Chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,7-naphthyridine

HRID 1618778Notes

Reaction equation

HRID 1618778 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.[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Sn](CCCC)(CCCC)CCCC)[CH:16]=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:17]2[CH:16]=[C:15]([CH3:14])[CH:20]=[CH:19][N:18]=2)[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 112227754-Methyl-2-(tributylstannyl)pyridineHCID 596315492,4-Dichloro-3-methyl-1,7-naphthyridine

Product 1

HCID 672850504-Chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared according to procedure E using 2,4-dichloro-3-methyl-1,7-naphthyridine (100 mg, 0.469 mmol), 4-methyl-2-(tributylstannyl)pyridine (215 mg, 0.563 mmol) and Pd(PPh3)4 (54.2 mg, 0.047 mmol). After purification 4-chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,7-naphthyridine was obtained as a white solid. Mass Spectrum (ESI) m/e=270.0 (M+1).

Workup

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

Sources & evidence

ORD record
ord-79ddae6a4f974053aaea7bca08987452
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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