Sodium Carbonate → HCID 58438736, compound

HRID 217462Notes

Reaction equation

HRID 217462 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([CH:21]=[O:22])[CH2:17][O:18]3)=[CH:13][CH:12]=2)[S:5][C:6]=1[CH2:7][CH3:8].[F:23][C:24]([F:36])([F:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1OB(O)O.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH4+].[Cl-]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:7]([C:6]1[S:5][C:4]([CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([CH:21]=[O:22])[CH2:17][O:18]3)=[CH:13][CH:12]=2)=[CH:3][C:2]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]([F:36])([F:35])[F:23])[CH3:8]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 22049664HCID 22049664, compoundHCID 58438974HCID 58438974, compound

Product 1

HCID 58438736HCID 58438736, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-[(4-bromo-5-ethyl-2-thienyl)methoxy]-2H-chromene-3-carbaldehyde (150 mg) in dioxane (4.5 mL) were added [2-(trifluoromethyl)phenyl]boric acid and a 2 M aqueous Na2CO3 solution at 25° C. Then, to the reaction mixture were added palladium acetate (4.44 mg) and PPh3 (20.75 mg), followed by warming to 100° C. and stirring for 5 hours. To the reaction liquid was added a saturated aqueous NH4Cl solution (30 mL), followed by extraction with EtOAc (30 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 80:20) to obtain 7-({5-ethyl-4-[2-(trifluoromethyl)phenyl]-2-thienyl}methoxy)-2H-chromene-3-carbaldehyde (134.8 mg) as a pale yellow liquid.

Workup

  1. customat 25° C
  2. customTo the reaction liquid
  3. extractionfollowed by extraction with EtOAc (30 mL) three times
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 80:20)

Sources & evidence

ORD record
ord-4112dde0ae3e4cafbb92ff62baaf0871
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

Loading…