Sodium Carbonate → HCID 67285530, compound

HRID 1618776Notes

Reaction equation

HRID 1618776 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.[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](=[N:5][CH: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 220826612,4-Dichloro-3-methyl-1,8-naphthyridineHCID 44717403(5-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 67285530HCID 67285530, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Prepared according to procedure F using 2,4-dichloro-3-methyl-1,8-naphthyridine (165 mg, 0.774 mmol), 5-fluoropyridine-3-boronic acid (109 mg, 0.774 mmol), sodium carbonate (144 mg, 1.75 mmol) and Pd(PPh3)4 (89 mg, 0.077 mmol). Purification by column chromatography (hexanes:EtOAc, 1:0 to 1:1 as eluant) gave 4-chloro-2-(5-fluoropyridin-3-yl)-3-methyl-1,8-naphthyridine. Mass Spectrum (ESI) m/e=274.0 (M+1).

Workup

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

Sources & evidence

ORD record
ord-414c171686a5428696145c48f05b9cfa
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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