Potassium Carbonate → 1-(2-Hydroxyethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][OH:10])[CH:7]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1B(O)O.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>>[OH:10][CH2:9][CH2:8][N:6]1[CH:7]=[C:2]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)[CH:3]=[CH:4][C:5]1=[O:11]Participants
Procedure
To a microwave vial with 5-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one (0.400 g, 2 mmol), 2-thiopheneboronic acid (0.800 g, 6 mmol), Potassium Carbonate (2 mL, 4 mmol) and 1,4-Dioxane (2.5 mL, 29 mmol) was added Palladium-Fibrecat. The vial was equipped with a stir bar and capped. The vial was placed into the CEM microwave for 20 minutes at 140° C., while 50 Watts of energy was supplied via Powermax. The progress of the reaction was monitored by LC/MS, which showed mostly desired product in the mixture. The mixture was diluted with CH2Cl2 (3 mL) and Water (2 mL). The organic layer was extracted with 3:1 CH2Cl2/MeOH (3×16 mL). Combined organics, dried over Sodium sulfate, filtered and concentrated in-vacuo. The crude was recrystallized from 5:1 CH2Cl2/MeOH and Hexanes to give the desired product as a light-yellow crystalline solid (0.280 g, 69% yield). MS (ESI pos. ion) m/z (MH+): 222. Calc'd exact mass for C11H11NO2S: 221. 1H NMR (300 MHz, CDCl3): 7.60 (s, 3H), 7.06 (s, 3H), 4.16 (s, 2H), 3.98 (s, 2H).
Workup
- customThe vial was equipped with a stir bar
- customcapped
Sources & evidence
- ORD record
- ord-7e1a4cf8586b41098d400fdd6cae2923
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314087B2
Reaction notes
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