Dimethylformamide → HCID 178436702, compound

Temperature

80 °C

Ethyl 6-hydroxy-5-iodonicotinate (200 mg, 0.682 mmol) was added with N,N′-dimethylformamide (4.1 mL) and water (1.4 mL). The resultant mixture was then added with tetrakis triphenylphosphine palladium (79 mg, 0.0682 mmol), vinylboronic acid (417 μL, 2.46 mmol) and sodium carbonate (433 mg, 4.09 mmol), and stirred at 80° C. for 20 minutes. Subsequently, the resultant mixture was further added with tetrakis triphenylphosphine palladium (79 mg, 0.0682 mmol) and vinylboronic acid (417 μL, 2.46 mmol), and stirred at 80° C. for 20 minutes. The reaction solution was filtered using celite and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (chloroform/acetone) and concentrated in vacuo. Ethyl 6-hydroxy-5-vinylnicotinate (95 mg, yield 72%) was obtained as a yellow oil.

1. stirringstirred at 80° C. for 20 minutes
2. filtrationThe reaction solution was filtered
3. extractionextracted with ethyl acetate
4. washSubsequently, the organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe obtained residue was purified
8. concentrationconcentrated in vacuo

ORD record

ord-ba2113af61234b2a9682c8026eea66fa

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153634B2