Cesium carbonate → HCID 44224665, compound

HRID 1914548Notes

Reaction equation

HRID 1914548 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.C(O)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343222-Chlorophenylboronic acidHCID 40012281HCID 40012281, compound

Product 1

HCID 44224665HCID 44224665, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

(5-Bromo-thiophen-3-yl)-piperidin-1-yl-methanone (75 mg, 0.27 mmol) was dissolved in dimethoxyethane (1 mL) and ethanol (1 mL). 2-Chlorophenylboronic acid (0.54 mmol), [1,1′-bis(diphenylphosphino)ferrocine]dichloropalladium (II) (0.014 mmol) and caesium carbonate (0.41 mmol) were added and the reaction mixture heated to 140° C. using microwave irradiation for 1 hour. The solvent was removed under vacuum and the residue dissolved in ethyl acetate. The organic solution was washed with water, dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by column chromatography on silica, eluting with 0%-25% ethyl acetate in petroleum ether. The fractions containing the desired product were concentrated under vacuum to give the title compound (48 mg). LCMS m/z 306.02 [M+H]+ R.T.=11.48 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.5 (m, 3H), 7.4 (s, 1H), 7.3-7.4 (m, 2H), 3.6 (m, 4H), 1.7-1.5 (m, 6H).

Workup

  1. custommicrowave irradiation for 1 hour
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe organic solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography on silica
  9. washeluting with 0%-25% ethyl acetate in petroleum ether
  10. additionThe fractions containing the desired product
  11. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-59db270bd57d4e839ed5d6d884cd997d
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

Loading…