Sodium Hydroxide → (2,6-difluorophenyl)-N-[5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)(2-pyridyl)]carboxamide

To a solution of 183 (30 mg, 0.12 mmol) in CH2Cl2 was added 4-dimethylaminopyridine (DMAP, 1.2 mg, 0.01 mmol), 2,6-difluorobenzol chloride (53 mg, 0.3 mmol) and diisopropylethylamine (DIEA, 62 mg, 0.48 mmol). The reaction mixture was stirred for 2 h at ambient temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with EtOAc. The organic solvent was removed in vacuo. The residue was dissolved in THF: MeOH (1:1) and added 1N NaOH (2 eq). The mixture was stirred for 10 min at ambient temperature. The reaction solution was concentrated in vacuo and residue was extracted with EtOAc. The crude product was purified by ISCO column and HPLC. Fractions containing pure product were combined and evaporated. The white solid 185 (18.2 mg, 40%) was obtained. LC-MS: calcd. for C21H16F2N2O3: 383 (M+1).

1. customThe reaction was quenched with saturated NaHCO3 (20 ml)
2. extractionextracted with EtOAc
3. customThe organic solvent was removed in vacuo
4. dissolutionThe residue was dissolved in THF: MeOH (1:1)
5. stirringThe mixture was stirred for 10 min at ambient temperature
6. concentrationThe reaction solution was concentrated in vacuo and residue
7. extractionwas extracted with EtOAc
8. customThe crude product was purified by ISCO column and HPLC
9. additionFractions containing pure product
10. customevaporated

ORD record

ord-5af5668acaaa48caa9eccb32e1691c1b

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120751B2