Sodium Carbonate → N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

温度

100 °C

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

1. customThe reaction mixture was quenched with water
2. extractionextracted with ether
3. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
4. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
5. customafforded the crude product as a red oil
6. customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)

ORDレコード

ord-577ce0bfa216420d91f2772d3771d42c

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063105B2