Dimethylformamide → HCID 46313806, compound

HRID 602106Notes

Reaction equation

HRID 602106 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.CN(C=O)C.C([O-])([O-])=O.[Cs+].[Cs+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2479875,6-Dichloronicotinic acidHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 46313806HCID 46313806, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 5,6-dichloronicotinic acid (500 mg, 2.60 mmol), 3-fluorophenylboronic acid (364 mg, 2.60 mmol), DMF (25 mL), 2 M Cs2CO3 (6 mL) and Pd(Ph3)4 (30.1 mg, 0.0026 mmol). The reaction mixture was heated to 90° C. for 3 hrs and then allowed to cool to rt. The mixture was diluted with ethyl acetate/water and the layers separated. The organic layer was washed with brine, dried (MgSO4) and the solvent removed to give a solid, which was purified by chromatography (silica, DCM/MeOH) to give the desired product, 5-chloro-6-(3-fluorophenyl)nicotinic acid (623 mg, 95%). LC/MS (M+H)=252 observed, 252.02 expected.

Workup

  1. temperatureto cool to rt
  2. customthe layers separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed
  6. customto give a solid, which
  7. customwas purified by chromatography (silica, DCM/MeOH)

Sources & evidence

ORD record
ord-be3f5e6ef78e4c5e94ed43b00ea68df9
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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