Ammonium Chloride → N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C(C1C=CC(S([N:36]=[N+:37]=[N-:38])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:36]([C:4]1[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[N+:37]=[N-:38]Participants
Procedure
To a −78° C. solution of N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide (1.34 g, 6.83 mmol) in tetrahydrofuran (25 mL) was added tert-butyl]ithium (1.31 mL of a 1.7 M solution, 20.5 mmol) drop wise. After 3 h at −78° C., 4-dodecylbenzenesulfonyl azide (3.60 g, 10.2 mmol) was added at the reaction was allowed to warm to room temperature. After 1 h, saturated aqueous NH4Cl was added, and the tetrahydrofuran was removed via rotary evaporator. Dichloromethane was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes, then 5%→42% EtOAc/hexanes) to give the title compound (0.275 g). MS 234.0 (M+1).
Workup
- waitAfter 1 h
- customthe tetrahydrofuran was removed via rotary evaporator
- additionDichloromethane was added
- customthe layers separated
- dry with materialThe combined organics were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-6b88e919b8e04bb2b80c0a83cb4de6a4
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452903B2
Reaction notes
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