tert-Butanol → (8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](C(O)=O)[CH:8]=[CH:7]2.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.CCOC(C)=O.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>>[C:45]([O:49][C:20](=[O:29])[NH:17][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=2)[N:10]=1)([CH3:48])([CH3:47])[CH3:46]Participants
6
Procedure
8-Bromo-[1,6]naphthyridine-2-carboxylic acid (1 equiv.) is suspended in tert-butanol (20 mL). Triethylamine (1.1 equiv.) and diphenylphosphoryl azide (1.1 equiv.) are added and the reaction is warmed to reflux. After refluxing for 2.5 hours, the reaction is allowed to cool and half the solvent is removed by rotary evaporation. The residue is dissolved in ethyl acetate (200 mL) and washed with saturated NaHCO3 (50 mL). The organic phase is dried over magnesium sulfate, filtered and concentrated to afford the crude product. Silica gel chromatography (1:1 EtOAc:hexanes) affords the desired BOC amine as a solid, LC/MS (M+H) 324.1.
Workup
- temperaturethe reaction is warmed to reflux
- temperatureAfter refluxing for 2.5 hours
- temperatureto cool
- customhalf the solvent is removed by rotary evaporation
- dissolutionThe residue is dissolved in ethyl acetate (200 mL)
- washwashed with saturated NaHCO3 (50 mL)
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto afford the crude product
Sources & evidence
- ORD record
- ord-a5fe6721cafd407ba80ebd8bdc039810
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282506B2
Reaction notes
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