Ammonium Chloride → N-(1-(tert-butyldimethylsilyloxy)-2-(6-octylbenzo[d]thiazol-2-yl)propan-2-yl)-2-methylpropane-2-sulfinamide

Temperatur

-78 °C

A toluene (2 mL) solution of 2-bromo-6-octylbenzo[d]thiazole (167 mg, 0.515 mmol) was cooled down to −78° C., then 2.5 N n-BuLi (0.2 mL, 0.515 mmol) was added to the mixture drop wise, and the mixture was stirred at −78° C. for 30 min. The toluene (2 mL) solution of (E)-N-(1-(tert-butyldimethylsilyloxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide (100 mg, 0.344 mmol) was cooled down to −78° C., then 2.0 N AlMe3 (0.26 mL, 0.515 mmol) was added to the mixture drop wise, and the mixture was stirred at −78° C. for 30 min. The mixture of (E)-N-(1-(tert-butyldimethylsilyloxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide was added to the mixture of the lithiated 2-bromo-6-octylbenzo[d]thiazole and stirred at −78° C. for 1 h. Then saturated NH4Cl solution was added to the mixture to quench the reaction. The mixture was extracted with EtOAc and purified by silica gel chromatography using PE/EA (5/1) to give is the title compound. (90 mg, 48%). EDI-MS (M+1): 539. 1H NMR (300 MHz, CDCl3) d 7.858 (d, 1H), 7.626 (s, 1H), 7.252 (s, 1H), 4.031 (d, 2H), 3.850 (d, 1H), 3.470 (s, 1H), 2.699 (t, 2H), 1.797 (s, 3H), 1.623 (t, 2H), 1.295-1.261 (m, 21H), 0.850 (s, 9H), 0.012 (s, 6H).

1. stirringthe mixture was stirred at −78° C. for 30 min
2. stirringstirred at −78° C. for 1 h
3. customto quench
4. customthe reaction
5. extractionThe mixture was extracted with EtOAc
6. custompurified by silica gel chromatography
7. customto give

ORD-Eintrag

ord-87be910832554c9ba51cb898e9592e47

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09181191B2