tert-Butanol → HCID 45789215, compound

HRID 887709Notes

Reaction equation

HRID 887709 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.C([N:30]([CH2:33]C)CC)C.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>>[C:35]([O:39][C:33](=[O:18])[NH:30][C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[Cl:1])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27358163-Chloropyridine-4-carboxylic acid

Product 1

HCID 45789215HCID 45789215, compound

Conditions

Temperature
100 °C

Procedure

3-Chloro-isonicotinic acid (3.0 g) was dissolved in tert-butanol (80 mL), diphenyl phosphoryl azide (5.24 g) and triethylamine (2.7 mL) were added and the reaction mixture was stirred at 100° C. for 5.5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuum and the residue was dissolved in ethyl acetate and water. The layers were separated and the aqueous layer was 2× extracted with ethyl acetate, the combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate 3:1, Rf=0.30) to afford 2.74 g of the title compound of the formula

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customThe layers were separated
  5. extractionextracted with ethyl acetate
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuum
  9. customThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate 3:1, Rf=0.30)

Sources & evidence

ORD record
ord-119a7193ef98446e862f63b6903c6197
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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