tert-Butanol → HCID 89666804, compound

HRID 2171245Notes

Reaction equation

HRID 2171245 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[N:44]=[CH:43][CH:42]=[N:41]2)=[N:33][CH:34]=[C:35]([CH:39]=1)C(O)=O>C1(C)C=CC=CC=1>[F:30][C:31]1[CH:39]=[C:35]([NH:3][C:6](=[O:20])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])[CH:34]=[N:33][C:32]=1[N:40]1[N:41]=[CH:42][CH:43]=[N:44]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 89666853HCID 89666853, compound

Product 1

HCID 89666804HCID 89666804, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (158 μl), tert-butanol, and DPPA (246 μl) were added to a toluene (5 ml) solution containing 5-fluoro-6-(2H-1,2,3-triazol-2-yl)nicotinic acid (198 mg) obtained in the 1st step, followed by stirring at 100° C. for 1 hour. The reaction solution was adjusted to room temperature and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1) and a white solid of tert-butyl (5-fluoro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)carbamate (94 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. customwas adjusted to room temperature
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-64ecee52591f440ea8b9204ff1ac60a4
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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