Potassium Carbonate → HCID 68841076, compound

HRID 491395Notes

Reaction equation

HRID 491395 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:11]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:30][O:31][C:32]1[N:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[CH3:30][O:31][C:32]1[N:37]=[CH:36][C:35]([C:7]2[CH2:8][CH2:9][N:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH:11]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 86618481HCID 86618481, compound

Product 1

HCID 68841076HCID 68841076, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4-(trifluoromethylsulfonyloxy)-2,3-dihydro-1H-pyrrole-1-carboxylate (200 mg, 0.57 mmol) in THF (10 mL) was purged with nitrogen for 10 minutes. The mixture was treated with K2CO3 (200 mg, 1.44 mmol), 6-methoxypyridin-3-ylboronic acid (100 mg, 0.66 mmol), tetrakis(triphenyl-phosphine)palladium (10 mg, 0.008 mmol), and water (100 μL). The reaction mixture was then heated to reflux for 16 hours. The reaction was treated with saturated aqueous NaHCO3 (20 mL) and then extracted with ethyl ether (20 mL). The organic layer was washed with saturated aqueous NaCl (20 mL), and then dried over Na2SO4. The crude mixture was filtered, concentrated and purified by flash chromatography (SiO2, 50% ethyl acetate/hexane) to afford the title compound (100 mg, 57%). 1HNMR (500 MHz, CDCl3) δ 8.05 (m, 1H), 7.55 (m, 1H), 7.30 (m, 5H), 6.66 (m, 1H), 5.98 (m, 1H), 5.13 (m, 2H), 4.44 (m, 2H), 4.30 (m, 2H), 3.86 (s, 3H).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with ethyl ether (20 mL)
  4. washThe organic layer was washed with saturated aqueous NaCl (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe crude mixture was filtered
  7. concentrationconcentrated
  8. custompurified by flash chromatography (SiO2, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ede0c70b4faf4eebb251f59542972b10
Source dataset
uspto-grants-2009_05
Patent number
US07531539B2

Reaction notes

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