tert-Butanol → (4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester
Reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.C([N:19]([CH2:22]C)CC)C.[C:24]([OH:28])([CH3:27])([CH3:26])[CH3:25].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1>CN(C=O)C>[C:24]([O:28][C:22](=[O:36])[NH:19][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[Br:1])=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)([CH3:27])([CH3:26])[CH3:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 4-Bromo-6-methoxyquinoline-3-carboxylic acid (34 g, 0.121 mole), triethylamine (141 mL) and tert-butanol (181 mL) in dry DMF (400 mL) was added diphenylphosphoryl azide (36.6 g, 28.6 mL, 0.133 mole). The mixture was heated at 100° C. for 1 h (see Note), then cooled and concentrated. The residue was dissolved in CH2Cl2 and washed with water (some insoluble material was removed by filtration). The aqueous phase was extracted with dichloromethane and the combined organics were dried (Na2SO4) and concentrated. Chromatography on silica gel (1 kg, 1:1 ether/light petroleum ether) gave the carbamate (22.7 g, 53%): MS (ES) m/e 309/311 (M+H)+, 354/6.
Workup
- temperaturecooled
- concentrationconcentrated
- dissolutionThe residue was dissolved in CH2Cl2
- washwashed with water (some insoluble material
- customwas removed by filtration)
- extractionThe aqueous phase was extracted with dichloromethane
- dry with materialthe combined organics were dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ba57edd1b47e4d0899628028abc86b3d
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511035B2
Reaction notes
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