Water → HCID 67240006, compound

HRID 473418Notes

Reaction equation

HRID 473418 reaction equation
Cl[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([Cl:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.O.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.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:17][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=[C:2]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([F:19])[CH:25]=2)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 77231055HCID 77231055, compound

Product 1

HCID 67240006HCID 67240006, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of ethyl 2,4-dichloro-1,5-naphthyridine-3-carboxylate (1.0 g, 3.69 mmol) in acetonitrile:water (7 mL:2 mL) was added Pd (PPh3)4 (0.426 g, 0.369 mmol), 3-fluorophenylboronic acid (0.568 g, 4.06 mmol) and sodium carbonate (0.782 g, 7.38 mmol) and the reaction was heated at reflux for 6 h. After this time the reaction was cooled to rt and partitioned between EtOAc (80 mL) and water (30 mL). The separated organic layer was dried over MgSO4, filtered and concentrated in vacuo. The mixture was purified by column chromatography on silica gel using a gradient from 1:0 to 4:1 of hexane:EtOAc to give ethyl 4-chloro-2-(3-fluorophenyl)-1,5-naphthyridine-3-carboxylate as a white solid: LC-MS (ESI) m/z 331.0 [M+H]+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 6 h
  3. custompartitioned between EtOAc (80 mL) and water (30 mL)
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe mixture was purified by column chromatography on silica gel using a gradient from 1:0 to 4:1 of hexane

Sources & evidence

ORD record
ord-232011d23e8044c58502bfbdc441b453
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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