Sodium Carbonate → 4-Chloro-2-(5-fluoropyridin-3-yl)-3-methyl-1,7-naphthyridine

HRID 1618779Notes

Reaction equation

HRID 1618779 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.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[N:19][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>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:18]=[N:19][CH:20]=[C:15]([F:14])[CH:16]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 596315492,4-Dichloro-3-methyl-1,7-naphthyridine

Product 1

HCID 672851084-Chloro-2-(5-fluoropyridin-3-yl)-3-methyl-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared according to procedure F using 2,4-dichloro-3-methyl-1,7-naphthyridine (100 mg, 0.469 mmol), 5-fluoropyridine-3-boronic acid (66.1 mg, 0.469 mmol), sodium carbonate (87 mg, 0.821 mmol) and Pd(PPh3)4 (54.2 mg, 0.047 mmol). Product used without further purification in the next step. Mass Spectrum (ESI) m/e=274.0 (M+1).

Workup

  1. customPrepared
  2. customProduct used without further purification in the next step

Sources & evidence

ORD record
ord-876e54d216024e50824d4ace2eae4f6b
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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