tert-Butanol → HCID 89546817, compound

HRID 1620092Notes

Reaction equation

HRID 1620092 reaction equation
C([N:3]([CH2:6]C)CC)C.[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])=CC=1.[F:30][C:31]1[C:32]([N:40]2[CH:44]=[CH:43][CH:42]=[N:41]2)=[N:33][CH:34]=[C:35]([CH:39]=1)C(O)=O>O.C1(C)C=CC=CC=1>[C:8]([O:12][C:6](=[O:20])[NH:3][C:35]1[CH:34]=[N:33][C:32]([N:40]2[CH:44]=[CH:43][CH:42]=[N:41]2)=[C:31]([F:30])[CH:39]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68620679HCID 68620679, compound

Product 1

HCID 89546817HCID 89546817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Triethylamine (193 μl), tert-butanol (227 μl), and DPPA (525 μl) were added to a toluene (5 ml) solution containing 5-fluoro-6-(1H-pyrazol-1-yl)nicotinic acid (330 mg), followed by reflux for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 3:1), and a white solid of tert-butyl(5-fluoro-6-(1H-pyrazol-1-yl)pyridin-3-yl)carbamate (210 mg) was thus obtained.

Workup

  1. temperatureby reflux for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 3:1)

Sources & evidence

ORD record
ord-961ba8b6afae4386884fceafe5e9cf11
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

Loading…