Triphenylphosphine → 2-(1-Azidoethyl)-3-phenyl-3H-imidazo[4,5-c]pyridine

HRID 243046Notes

Reaction equation

C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]1([N:24]2[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]2[CH:33](O)[CH3:34])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(Cl)Cl>[N:15]([CH:33]([C:25]1[N:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:27]=2[N:26]=1)[CH3:34])=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 20 °C

Procedure

Diphenylphosphoryl azide (1.12 g, 4.06 mmol) and then diisopropyl azadicarboxylate (1.37 g, 6.77 mmol) were added to a stirred solution of 1-(3-phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanol (0.81 g, 3.39 mmol) and triphenylphosphine (1.78 g, 6.77 mmol) in dioxane (50 mL) at 0° C. under nitrogen. The reaction mixture was stirred at 20° C. for 16 h then diluted with DCM to dissolve all the material. This was loaded onto an Isolute® SCX-2 cartridge and washed with methanol and the product eluted with 2M NH3/MeOH then concentrated in vacuo. The residue was purified by chromatography (SiO2 0-4% (2M ammonia in methanol) in DCM) to give the title compound as a colourless oil (1.48 g, contaminated with triphenylphosphine oxide). LCMS (method H): Rt 1.79 min, [M+H]+ 265.

Workup

dissolutionto dissolve all the material
washwashed with methanol
washthe product eluted with 2M NH3/MeOH
concentrationthen concentrated in vacuo
customThe residue was purified by chromatography (SiO2 0-4% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record: ord-872647d2aca6430190a6b568d8989ac0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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