1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin

HRID 1789834Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19](Br)=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([Si:28](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:27])([CH3:26])[CH3:25].C([O:48][CH2:49][CH3:50])C.[F-].[K+].Cl[CH2:54]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]([N:8]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:49]([CH3:50])([CH3:54])[O:48][SiH2:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-4-methylpyridin (15.0 g, 38.70 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (25.4 g, 58.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2dichloroethane (50 mL) was stirred at 90° C. for two days. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (40 mL). The mixture was stirred vigourously for 30 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 95:5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin (10.0 g, 57%).

Workup

filtrationfiltered
washThe organic phase was washed with water
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-11b564af92244385904b20e883187645
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071175B1

Reaction notes

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