Sodium Carbonate → Carbamic acid, (4-(4-formylphenyl)-2-pyridinyl)-, 1,1-dimethylethyl ester

Tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.08 mmol, 0.05 equiv) was added to a deoxygenated mixture of tert-butyl 4-iodopyridin-2-ylcarbamate (1-1, 0.500 g, 1.56 mmol, 1 equiv), 4-formylphenyl boronic acid (351 mg, 2.34 mmol, 1.50 equiv), and aqueous saturated sodium carbonate solution (2.0 M, 2.3 mL, 4.7 mmol, 3.0 equiv) in dioxane (15 mL), and the resulting mixture was heated at reflux for 18 h. The reaction mixture was cooled then concentrated. The residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL). The organic layer was dried over sodium sulfate, and concentrated to give tert-butyl 4-(4-formylphenyl)pyridin-2-ylcarbamate (2-1) as an off-white solid. LRMS m/z (M+H) Calcd: 242.2 (minus t-Bu), 199.2 (minus Boc); found 243.0 and 199.0.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 18 h
3. temperatureThe reaction mixture was cooled
4. concentrationthen concentrated
5. customThe residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (100 mL)
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated

ORD-Eintrag

ord-6745573145bb4ac7be1e9bf674f2a298

Quelldatensatz

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07125888B2