Triphenylphosphine → 2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine
Reaction equation
[C:1]1([C:7]2[N:8]=[N:9][NH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][CH2:20][CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH2:21][CH2:20][C:19]#[C:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 5-phenyl-2H-tetrazole (330 mg, 2.2 mmol), 4-(pyridin-2-yl)but-3-yn-1-ol (220 mg, 1.49 mmol) and triphenylphosphine polymer supported (750 mg, 2.2 mmol, loading 3 mmol/g) were dissolved DCM (3 mL) and stirred at 0° C. Diisoprpylazodicarboxylate (452 mg, 2.2 mmol) was added dropwise, at 0° C. over a period of 30 min The reaction mixture was then warmed to room temperature and stirred over night. The reaction mixture was filtered through celite and the cake was washed with DCM. The combined organic layers were washed with aqueous ammoniac, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 209 mg of 2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine (Yield: 51%) as a pink powder (M.P.=71-73° C.).
Workup
- additionwas added dropwise, at 0° C. over a period of 30 min The reaction mixture
- temperaturewas then warmed to room temperature
- stirringstirred over night
- filtrationThe reaction mixture was filtered through celite
- washthe cake was washed with DCM
- washThe combined organic layers were washed with aqueous ammoniac, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)
Sources & evidence
- ORD record
- ord-771725ecc09441d494661c29d66887de
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101637B2
Reaction notes
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