Ammonium Chloride → N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

HRID 1671581Notes

Reaction equation

HRID 1671581 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([Li])(C)(C)C.C(C1C=CC(S([N:41]=[N+:42]=[N-:43])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:41]([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+:42]=[N-:43]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 109151434-Dodecylbenzenesulfonyl azideHCID 22293237N-(5-Fluoropyridin-2-yl)pivalamideHCID 178418306HCID 178418306, compound

Product 1

HCID 22293288N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamideYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-butyllithium (1.31 mL of a 1.7 M solution, 20.5 mmol) dropwise. 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).

Workup

  1. waitAfter 1 h
  2. customthe tetrahydrofuran was removed via rotary evaporator
  3. additionDichloromethane was added
  4. customthe layers separated
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

Sources & evidence

ORD record
ord-0b025a906a324f5f8f43caa93bb3775c
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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