Potassium Carbonate → HCID 86704611, compound
Reaction equation
[OH:1][C:2]1[C:3](I)=[C:4](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:17]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[OH:1][C:2]1[C:3]([CH3:17])=[C:4](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of methyl (2E)-3-(3-hydroxy-2-iodo-4-methoxyphenyl)prop-2-enoate (2.0 g, 5.99 mmol) in methanol (30 ml) was added trimethylboroxine (1.683 ml, 11.97 mmol), potassium carbonate (2.482 g, 17.96 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (1.170 g, 1.796 mmol). The mixture was stirred overnight at 90° C. The solution was then filtered through a plug of silica gel (eluting with ethyl acetate), concentrated in vacuo and the residue was purified via column chromatography on a Biotage 65i column eluting with hexanes (1 CV) followed by a gradient of 0-50% ethyl acetate in hexanes (over 6.7 CVs) to furnish the desired compound. 1H NMR (CDCl3, 500 MHz) δ 7.95 (d, J=15.9 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 6.27 (d, J=15.8 Hz, 1H), 3.91 (s, 3H), 3.80 (s, 3H), 2.34 (s, 3H).
Workup
- filtrationThe solution was then filtered through a plug of silica gel (eluting with ethyl acetate)
- concentrationconcentrated in vacuo
- customthe residue was purified via column chromatography on a Biotage 65i column
- washeluting with hexanes (1 CV)
Sources & evidence
- ORD record
- ord-0ac8df55732243ae97347ad9f93d074c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221834B2
Reaction notes
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