Sodium Carbonate → 2-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-one

HRID 423388Notes

Reaction equation

HRID 423388 reaction equation
Br[C:2]1[S:11][C:5]2[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.CO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[S:11][C:5]3[C:6](=[O:10])[NH:7][CH2:8][CH2:9][C:4]=3[CH:3]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 513419322-Bromo-5,6-dihydrothieno(2,3-c)pyridin-7(4H)-one

Product 1

HCID 666730692-(4-Fluoro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridine-7-oneYield 75.2%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Add tetrakis(triphenylphosphine) palladium(0) (0.075 g, 0.065 mmol) to a degassed solution of 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.5 g, 2.15 mmol), 4-fluorophenylboronic acid (0.30 g, 2.15 mmol), and sodium carbonate (0.46 g, 4.30 mmol) in N,N-dimethylformamide (21 mL), methanol (5 mL) and water (1 mL). Heat the reaction at 90° C. for 16 h. Allow the reaction to cool to RT and pour into water (75 mL). Filter the resulting solid and dry in vacuo at 80° C. to give 0.40 g (75%) of the title compound. MS/ES m/z 248.0 [M+H]+.

Workup

  1. temperatureHeat
  2. customthe reaction at 90° C. for 16 h
  3. customthe reaction
  4. filtrationFilter the resulting solid
  5. customdry in vacuo at 80° C.

Sources & evidence

ORD record
ord-5137d9633b894ee8917f353ae35f17a5
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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