tert-Butanol → (2-Bromo-Pyridin-3-Yl)-Carbamic Acid Tert-Butyl Ester
Reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[Br:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1C(O)=O.C([N:30]([CH2:33]C)CC)C.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:39][C:33](=[O:8])[NH:30][C:20]1[C:19]([Br:18])=[N:27][CH:26]=[CH:25][CH:24]=1)([CH3:38])([CH3:37])[CH3:36]Participants
5
Procedure
Diphenylphosphorylazide was added to a solution of 2-bromonicotinic acid (15.0 g, 74.0 mmol) and triethylamine (11.4 mL, 81.4 mmol) in 140 mL of anhydrous tert-butanol. The reaction mixture was stirred under reflux for 2 hours, cooled to room temperature, and concentrated in vacuo. The residue was dissolved in 150 mL of ethyl acetate and washed with three 50 mL portions of water, three 50 mL portions of saturated aqueous sodium bicarbonate, and with two 50 mL portions of brine. The organic layer was dried over magnesium sulfate (MgSO4), filtered, and concentrated in vacuo. The residue crystallized upon standing to give 15.3 g of the title product (76% yield).
Workup
- temperatureunder reflux for 2 hours
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in 150 mL of ethyl acetate
- washwashed with three 50 mL portions of water, three 50 mL portions of saturated aqueous sodium bicarbonate
- dry with materialThe organic layer was dried over magnesium sulfate (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue crystallized
Sources & evidence
- ORD record
- ord-4fd1d984c58047329706886d85be8377
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741897B2
Reaction notes
Loading…