Triphenylphosphine → HCID 17974505, compound

HRID 2252325Notes

Reaction equation

HRID 2252325 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([CH:21]([CH3:23])[CH3:22])=[N:19][N:20]=2)[CH:17]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[CH:21]([C:18]1[N:16]2[CH:17]=[C:12]([S:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[CH2:4][NH2:1])[CH:13]=[CH:14][C:15]2=[N:20][N:19]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 17974512HCID 17974512, compound

Product 1

HCID 17974505HCID 17974505, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(2-Azidomethyl-phenylsulfanyl)-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine (228.0 mg, 0.70 mmol) in THF (2.3 mL) under N2 was added triphenylphosphine (220.0 mg, 0.84 mmol) and water (15.0 μL, 0.84 mmol). The reaction was stirred at ambient temperature under N2 for 12 hours, then warmed to 50° C. for 6 hours. To the reaction mixture was diluted with water, and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (10-100% methanol/ethyl acetate), followed by trituration with ethyl acetate/hexane to give the title compound (127 mg, 61%).

Workup

  1. temperaturewarmed to 50° C. for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (10-100% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-c7911e0c84c14990ab61cc4f67ecd491
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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