4-Methyl-2-(tributylstannyl)pyridine → 4-Chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,8-naphthyridine

HRID 1618744Notes

Reaction equation

HRID 1618744 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.[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](=[N:5][CH: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 220826612,4-Dichloro-3-methyl-1,8-naphthyridine

Product 1

HCID 672846184-Chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,8-naphthyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared according to procedure E and using 2,4-dichloro-3-methyl-1,8-naphthyridine (500 mg, 2.347 mmol), 4-methyl-2-(tributylstannyl)pyridine (897 mg, 2.347 mmol) and Pd(PPh3)4 (271 mg, 0.235 mmol). Purification by column chromatography (hexanes:EtOAc, from 1:0 to 1:2) gave 4-chloro-3-methyl-2-(4-methylpyridin-2-yl)-1,8-naphthyridine. Mass Spectrum (ESI) m/e=270.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (hexanes:EtOAc, from 1:0 to 1:2)

Sources & evidence

ORD record
ord-e0d06df1a2e94b2781d34f1a7318b0f7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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