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

HRID 243042Notes

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

Participants

Conditions

Temperature: 20 °C

Procedure

Diphenylphosphoryl azide (0.50 g, 1.81 mmol) and diisopropyl azadicarboxylate (0.61 g, 3.01 mmol) were added to a stirred solution of 1-(1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)ethanol (0.36 g, 1.50 mmol) and triphenylphosphine (0.79 g, 3.01 mmol) in dioxane (15 mL) at 0° C. under nitrogen. After addition the mixture was stirred at 20° C. for 16 h. Additional diphenyl phosphoryl azide (0.25 g, 0.91 mmol), triphenylphosphine (0.40 g, 1.53 mmol) and diisopropyl azadicarboxylate (0.30 g, 1.48 mmol) were added and the resultant mixture stirred at 20° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound as an oil (0.60 g, contaminated with triphenylphosphine oxide). LCMS (method H): Rt 1.86 min, [M+H]+ 265

Workup

additionAfter addition the mixture
concentrationThe reaction mixture was concentrated in vacuo
customthe residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record: ord-a6babf4ab61d4ab0a429f8b7d8692f7e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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