Dimethylformamide → HCID 45725783, Verbindung

To a solution of 5-bromo-2-iodobenzoic acid (1-1, 500 mg, 1.529 mmol, 1.0 equiv) in dichloromethane (8 mL) was added catalytic DMF (0.012 mL, 0.153 mmol, 0.1 equiv) and oxalyl chloride (0.161 mL, 1.835 mmol, 1.2 equiv) at 0° C. The reaction mixture was stirred for 1 hour and concentrated. The crude residue was dissolved in dichloromethane (15 mL) and to the reaction was added 3,4-dimethoxybenzylamine (281 mg, 1.682 mmol, 1.2 equiv), and TEA (0.682 mL, 4.59 mmol, 3.0 equiv) at 0° C. After stirring for 10 min, the mixture was removed from the cold bath, diluted with DCM and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 100% EtOAc in hexanes) to afford the product (1-2) as a tan solid. ESI+ MS [M+H]− C16H15BrINO3: 476.9 found, 476.1 required.

1. concentrationconcentrated
2. dissolutionThe crude residue was dissolved in dichloromethane (15 mL) and to the reaction
3. stirringAfter stirring for 10 min
4. customthe mixture was removed from the cold bath
5. additiondiluted with DCM
6. washwashed with water
7. dry with materialThe organic phase was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude material was purified by gradient elution on silica gel (0 to 100% EtOAc in hexanes)

ORD-Eintrag

ord-62c4eb93872e471580341657998f9c07

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399494B2