Potassium Carbonate → ethyl 7-(2-furyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854886Notes

Reaction equation

HRID 854886 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 69517680ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69518409ethyl 7-(2-furyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 21%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The ethyl 7-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 9a, Step 2 (2.0 g, 5.02 mmol), 2-furylboronic acid (0.62 g, 5.52 mmol), K2CO3 (2.08 g, 15.06 mmol), and PdCl2(PPh3)2 (106 mg, 0.15 mmol) were mixed in dioxane (20 mL) in a sterling bomb. Carbon monoxide was bubbling to 40 psi. The reaction was heated to 80° C. for 12 h. After filtration, the reaction was quenched with NH4Cl and extracted with EtOAc. The organic layer was washed and dried over MgSO4. The filtrate was evaporated and dried in vacuo to afford crude which was purified Biotage Chromatography with 10 to 20% ethyl acetate in hexane to give yellow solid (350 mg, 21%): LCMS m/z 339.05 (M+H). 1H NMR (CDCl3/300 MHz) 7.74 (s, 1H), 7.51 (s, 1H), 8.97 (m, 3H), 6.76 (d, 1H, J=3.3 Hz), 6.51 (m, 1H), 5.73 (q, 1H, J=6.9 Hz), 4.34 (m,2H), 1.36 (t, 3H, J=7.2 Hz).

Workup

  1. customCarbon monoxide was bubbling to 40 psi
  2. filtrationAfter filtration
  3. customthe reaction was quenched with NH4Cl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed
  6. dry with materialdried over MgSO4
  7. customThe filtrate was evaporated
  8. customdried in vacuo
  9. customto afford crude which
  10. customwas purified Biotage Chromatography with 10 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5bc26005c1b4475992ea3105f6e94e4f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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