Sodium Carbonate → 4-Fluoro-3-(5-formylpyridin-2-yl)benzamide

HRID 561353Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[C:10]([C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17](B(O)O)[CH:18]=1)(=[O:12])[NH2:11].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO>[F:22][C:16]1[CH:17]=[CH:18][C:13]([C:10]([NH2:11])=[O:12])=[CH:14][C:15]=1[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-bromo-3-pyridinecarboxaldehyde (336 mg, 1.80 mmol) in DME (8 mL) and EtOH (4 mL) under argon, was added (5-carbamoyl-2-fluorophenyl)boronic acid (300 mg, 1.64 mmol) followed by palladium tetrakistriphenylphosphine (190 mg, 0.16 mmol) and 2M Na2CO3 (4 mL). The mixture was heated to 80° C. for 16 h and then allowed to cool to rt. The mixture was partitioned between EtOAc (50 mL), THF (50 mL) and Na2CO3 (20 mL). The aqueous was extracted with EtOAc (50 mL) and the combined organics washed with brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM) to give the title compound: RT=2.50 min; m/z (ES+)=245.0 [M+H]+.

Workup

temperatureto cool to rt
customThe mixture was partitioned between EtOAc (50 mL), THF (50 mL) and Na2CO3 (20 mL)
extractionThe aqueous was extracted with EtOAc (50 mL)
washthe combined organics washed with brine (30 mL)
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customthe residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM)

Sources & evidence

ORD record: ord-d5279430e619446fa15f96da43a65166
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063247B2

Reaction notes

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