1,2-Dichloroethane → tert-butyl N-[5-(2-tert-butylsilyloxypropan-2-yl)-6-methyl-2-pyridinyl]carbamate

HRID 1789858Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[C:10]([CH3:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([Si:21](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:20])([CH3:19])[CH3:18].C([O:41][CH2:42][CH3:43])C.[F-].[K+].Cl[CH2:47]CCl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:42]([CH3:43])([CH3:47])[O:41][SiH2:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:10]([CH3:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (5-bromo-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (27.5 g, 95.8 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (43.5 g, 100.2 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) in 1,2-dichloroethane (350 mL) was stirred at reflux for 48 h. Additional bis(triphenylphosphine)palladium(II) dichloride (1.00 g, 1.40 mmol) was added every 12 h. The mixture was cooled to 0° C. and diethyl ether (300 mL) was added followed by saturated aqueous potassium fluoride (100 mL). The mixture was stirred vigourously for 60 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 1:99) gave [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (15 g, 47%).

Workup

temperatureat reflux for 48 h
filtrationfiltered
washThe organic phase was washed with water
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-184708061ceb4f5cb122024729392cba
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071175B1

Reaction notes

Loading…