Sodium Carbonate → 1-(1-Hydroxypropan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one

HRID 1878704Notes

Reaction equation

HRID 1878704 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:12])[N:6]([CH:8]([CH3:11])[CH2:9][OH:10])[CH:7]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:10][CH2:9][CH:8]([N:6]1[CH:7]=[C:2]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)[CH:3]=[CH:4][C:5]1=[O:12])[CH3:11]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 580703425-Bromo-1-(1-hydroxypropan-2-yl)pyridin-2(1H)-one

Product 1

HCID 598430661-(1-Hydroxypropan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-oneYield 29%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-1-(1-hydroxypropan-2-yl)pyridin-2(1H)-one (0.51 g, 2.2 mmol) and 2-thiopheneboronic acid (0.28 g, 2.2 mmol) in 30 mL of dioxane was added 6 mL of 1N Na2CO3 followed by 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.16 g, 0.22 mmol). The reaction was heated to 90° C. for 12 hours. The mixture was then diluted with 30 mL of water and 80 mL of EtOAc. The organic phase was separated, washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was obtained as a greenish semi-solid (0.15 g, 29% yield). MS (ESI pos. ion) m/z (MH+): 236.0. Calc'd Exact Mass for C12H13NO2S: 235.07.

Workup

  1. customThe organic phase was separated
  2. washwashed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78660626cb8848ea8030f6d17c3e4913
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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