tert-Butanol → Tert-butyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate

HRID 1802185Notes

Reaction equation

HRID 1802185 reaction equation
[F:1][C:2]1[C:3](C(O)=O)=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C([N:22]([CH2:25]C)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:28]C1C=CC=CC=1.[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[F:1][C:2]1[C:3]([NH:22][C:25](=[O:28])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 677761426-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

Product 1

HCID 67776795Tert-butyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamateYield 39.9%

Procedure

To a suspension of 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (495 mg, 1.92 mmol) and triethylamine (805 μl, 5.77 mmol) in tert-butanol (28.9 ml) is added diphenyl phosphorazidate (623 μl, 2.89 mmol) at 25° C. The resulting mixture is heated to reflux and stirred for 18 hours. The crude material is loaded on silicagel and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 30-100% as eluent affording tert-butyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (252 mg, 39.9%) as a light yellow solid. Mp.: 180-8° C. MS: m/z=329.2 (M+H+).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux
  3. custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record
ord-73dcf0719a944491b55f497de5e9ba64
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

Loading…