Potassium Carbonate → HCID 86680487, compound

HRID 1777446Notes

Reaction equation

HRID 1777446 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:10]([C:13]1[S:17][C:16](B(O)O)=[CH:15][CH:14]=1)(=[O:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:10]([C:13]1[S:17][C:16]([C:2]2[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:15][CH:14]=1)(=[O:12])[CH3:11]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 4143377(5-Acetylthiophen-2-yl)boronic acidHCID 130240275-Bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 86680487HCID 86680487, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-1-methylpyridin-2(1H)-one (0.2 g, 1.06 mmol) in 1,4-dioxane (5 mL) and water (2 mL), (5-acetylthiophen-2-yl)boronic acid (0.2 g, 1.27 mmol), tetrabutyl ammonium bromide (0.034 g, 0.16 mmol), K2CO3 (0.4 mL, 3.19 mmol) and Pd(PPh3)2Cl2 (0.18 g, 1.59 mmol) were added under argon. The mixture was purged with argon for 10 min and heated to 100° C. for 1 h. The reaction mixture was filtered through Celite® reagent, the filtrate concentrated, the residue extracted with EtOAc (2×100 mL), and washed with water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to obtain crude product. The crude product was purified by Biotage IsoleraOne® column purifier (80% ethyl acetate in hexane) and obtained as yellow viscous liquid (0.15 g, 62% yield). 1H NMR (400 MHz, CDCl3): δ 7.69-7.58 (m, 3H), 7.08 (d, 1H), 6.65 (d, 1H), 3.61 (s, 3H), 2.54 (s, 3H); LC-MS m/z calculated for M+H+ 234.05. found 234.1.

Workup

  1. customThe mixture was purged with argon for 10 min
  2. filtrationThe reaction mixture was filtered through Celite® reagent
  3. concentrationthe filtrate concentrated
  4. extractionthe residue extracted with EtOAc (2×100 mL)
  5. washwashed with water (100 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude product
  10. customThe crude product was purified by Biotage IsoleraOne® column purifier (80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6c08ae5e4dda4043a8f5a001ab9a9d89
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

Loading…