Nitrogen → HCID 13837878, compound

Temperature

-78 °C

A solution of oxindole 9 (6.25 g, 47 mmol) in THF (500 ml) was cooled to −78° C. and to it a solution of sodium hexamethyldisilazide (43 g, 235 mmol) in THF (300 ml) was added drop wise under N2 atmosphere. After stirring at −78° C. for 45 min, N-methylbis(2-chloromethyl)amine hydrochloride (9 g, 47 mmol) was added, as a solid. The reaction mixture was stirred at −78° C. for 1 h and at room temperature for 24 h. After quenching with H2O (90 ml), the mixture was extracted with ethyl acetate (3×100 ml). The organic extracts were washed with brine (25 ml), dried and the solvent removed in vacuo. Silica gel chromatography (5-50% MeOH/CH2Cl2, gradient) gave 6 g (57%) of 10 as a solid. 1HNMR (CD3OD, 400 MHz) δ 1.84 (m, 2H); 2.51 (m, 2H); 2.62 (s, 3H); 3.02 (m, 2H); 3.37 (m, 2H); 6.82 (d, 1H, J=7.68 Hz); 6.94 (t, 1H, J=7.58 Hz); 7.12 (t, 1H, J=7.7 Hz); 7.26 (d, 1H, J=9 Hz); 9.27 (br s, 1H).

1. stirringThe reaction mixture was stirred at −78° C. for 1 h and at room temperature for 24 h
2. customAfter quenching with H2O (90 ml)
3. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
4. washThe organic extracts were washed with brine (25 ml)
5. customdried
6. customthe solvent removed in vacuo

ORD record

ord-adf16c1c8d114034bda07aa9a3ef725f

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084609B2