Bromoacetyl bromide → 2-bromo-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]acetamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[C:6]([CH2:8][NH2:9])[CH:7]=1.CCN(C(C)C)C(C)C.[Br:24][CH2:25][C:26](Br)=[O:27]>C1COCC1.CCOC(C)=O>[Br:24][CH2:25][C:26]([NH:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[N:13][N:12]=[N:11]1)=[O:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 1-[5-chloro-2-(1H-tetraazol-1-yl)phenyl]methanamine (150 mg, 0.72 mmol) and Hünig's base (137 μL, 0.79 mmol) in anhydrous THF (3.3 mL) at 0° C. was added dropwise bromoacetyl bromide (69 μL, 0.79 mmol). The resulting orange-yellow suspension was stirred under N2 atmosphere at 0° C. for 20 min. The mixture was diluted with EtOAc and washed twice with H2O, twice with saturated aqueous NaHCO3 and once with brine. The organic layer was dried (anhydrous Na2SO4), filtered and concentrated to a brown oil. Silica gel chromatography (70% EtOAc-hexanes) afforded the title compound as a yellow oil which slowly formed a tan foam after drying in vacuo. 1H NMR (400 MHz, CDCl3): δ 8.95 (s, 1 H), 7.70 (d, J=2.2 Hz, 1 H), 7.50 (dd, J=2.0, 8.4 Hz, 1 H), 7.30 (d, J=8.4 Hz, 1 H), 7.21 (br s, 1 H), 4.29 (d, J=6.4 Hz, 2 H), 3.88 (s, 2 H).
Workup
- washwashed twice with H2O, twice with saturated aqueous NaHCO3 and once with brine
- dry with materialThe organic layer was dried (anhydrous Na2SO4)
- filtrationfiltered
- concentrationconcentrated to a brown oil
Sources & evidence
- ORD record
- ord-bbabf97ff7044c568fa6da4a7d2fbf79
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144899B2
Reaction notes
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