tert-Butyl acetate → HCID 66869285, compound

Pd2(dba)3 (928 mg, 1.01 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (838 mg, 2.13 mmol) are added at RT under an atmosphere of argon to a solution of lithium hexamethyl disilazide in toluene (prepared by addition of n-BuLi (1.6 M in hexane, 24.3 ml, 38.85 mmol) to hexamethyl disilazane (6.27 g, 38.85 mmol) in toluene (100 ml) at −78° C.). The mixture is stirred at RT for 10 minutes, then it is cooled to −10° C. Acetic acid tert-butyl ester (4.12 g, 35.48 mmol) is added during 10 minutes. This mixture is canulated into a cold (−10° C.) solution of 1,3-dichloropyridine (5.00 g, 33.79 mmol) in toluene (40 ml). The mixture is warmed to RT and stirred for 2 h. TLC analysis indicated substantial conversion of starting material. Water was added, the resulting slurry is filtered, and the filtrate is extracted with EtOAc. The combined organic layers are dried over Na2SO4 and concentrated. Purification by FCC (hexane/EtOAc 100:0 to 92:8 to 85:15) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.39 (s, 9H), 3.47 (s, 2H), 7.58-7.60 (m, 1H), 8.31 (s,1H), 8.41-8.42 (m, 1H). ES+−MS: 228.3 [M+H]+.

1. temperatureit is cooled to −10° C
2. temperatureThe mixture is warmed to RT
3. stirringstirred for 2 h
4. filtrationthe resulting slurry is filtered
5. extractionthe filtrate is extracted with EtOAc
6. dry with materialThe combined organic layers are dried over Na2SO4
7. concentrationconcentrated
8. customPurification by FCC (hexane/EtOAc 100:0 to 92:8 to 85:15)

ORD record

ord-cce30bca58fd4a9fad9f74e58ffe8874

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07648989B2