Triethylamine → Ethyl (2,6-dibromo-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate

HRID 629934Notes

Reaction equation

[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([Br:17])[N:3]=1.C(N(CC)CC)C.Br[CH2:26][C:27]1[CH:41]=[CH:40][C:30]([CH2:31][P:32](=[O:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[CH:29][CH:28]=1>C(#N)C>[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:31][P:32]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])=[O:39])=[CH:40][CH:41]=2)[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([Br:17])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl (2,6-dibromo-3-nitropyridin-4-yl)carbamate (1 equiv.) (described in ref. 18, Preparation 67) in acetonitrile (0.40 M) was added triethyl amine (1.5 equiv.) and diethyl 4-(bromomethyl)benzylphosphonate (1.3 equiv.) (described in ref. 88, Ex 25 Step 1). The reaction mixture was then heated to 60° C. for 18 h. At this point the reaction mixture was allowed to cool to room temperature and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-5% MeOH/DCM to provide the title compound (38%) as a solid.

Workup

temperatureto cool to room temperature
customthe volatiles were removed in vacuo
customThe resulting residue was purified by a COMBIFLASH™ system

Sources & evidence

ORD record: ord-429a103333fe42548bbd9299f57f1e24
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315530B2

Reaction notes

Loading…