Triethylamine → 6-Fluoro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

HRID 1406684Notes

Reaction equation

HRID 1406684 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH:11]([CH3:13])[CH3:12])=[N:9][N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66977821Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Product 1

HCID 587839636-Fluoro-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridineYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 1 step c (0.41 g, 2.08 mmol), triphenylphosphine (763 mg, 2.91 mmol) and triethylamine (0.87 mL, 6.24 mmol) in THF (5 mL) at 0° C. was treated with 1,2-hexachloroethane (690 mg, 2.91 mmol). The reaction mixture was stirred at 0° C. for 40 min then at RT for 20 min, quenched with water, extracted twice with EtOAc, dried (Na2SO4), evaporated and purified twice by FCC (cyclohexane/EtOAc 1/0 to 1/1) to afford the title compound (274 mg, contaminated with 20% PPh3O, 58%) as a white solid. LCMS (method 1): Rt 2.58 min, m/z 180 [MH+].

Workup

  1. waitat RT for 20 min
  2. customquenched with water
  3. extractionextracted twice with EtOAc
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. custompurified twice by FCC (cyclohexane/EtOAc 1/0 to 1/1)

Sources & evidence

ORD record
ord-a53d3a73540f47b5b45d315176632ee6
Source dataset
uspto-grants-2014_12
Patent number
US08916708B2

Reaction notes

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