tert-Butanol → HCID 89546817, compound

HRID 340485Notes

Reaction equation

HRID 340485 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-361f0e6bb21d46b7a4d4c1132f181c92
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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