Ammonium Chloride → HCID 57619437, compound
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C([Li])CCC.CON(C)[C:28](=[O:30])[CH3:29].[Cl-].[NH4+]>O1CCCC1.CCCCCC.[Cl-].[Na+].O>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[N:6]=[CH:7][C:2]([C:28](=[O:30])[CH3:29])=[CH:3][CH:4]=2)=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
(5-Bromo-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-amine (17, 3.00 g, 9.06 mmol, prepared as described in Example 10, Scheme 12) was dissolved in tetrahydrofuran (80 mL). The reaction was cooled at −78° C. under an atmosphere of argon. 2.5 M n-butyllithium in hexane (10.9 mL) was added. The reaction was stirred at −78° C. for 60 minutes. N-Methoxy-N-methylacetamide (1.93 mL, 18.1 mmol) was added to the reaction, which was allowed to warm to room temperature. The reaction was poured into 1M ammonium chloride and brine and extracted with ethyl acetate. The organic portions were dried with anhydrous sodium sulfate, filtered and the filtrate was adsorbed onto silica. The mixture was purified by silica gel chromatography (ethyl acetate:hexanes) to provide the desired compound as an oil that crystallized to a white solid (620, 1.328 g, 50%), consistent with the compound structure by 1H-NMR and MS (ESI): [M+H+]+=295.3.
Workup
- temperatureto warm to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe organic portions were dried with anhydrous sodium sulfate
- filtrationfiltered
- customThe mixture was purified by silica gel chromatography (ethyl acetate:hexanes)
Sources & evidence
- ORD record
- ord-b9646e6191e547d6a3c8f8dc531e189a
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169250B2
Reaction notes
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