Trimethylsilylmethyl Azide → Methyl 3-(5-methylpyridin-2-yl)-5-(1-((trimethylsilyl)methyl)-1H-1,2,3-triazol-5-yl)benzoate

HRID 888386Notes

Reaction equation

HRID 888386 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[CH:2].[CH3:20][Si:21]([CH2:24][N:25]=[N+:26]=[N-:27])([CH3:23])[CH3:22]>C1C=CC=CC=1.C[C]1[C](C)[C](C)[C](C)[C]1C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[C:5]([CH:4]=[C:3]([C:1]3[N:25]([CH2:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[N:26]=[N:27][CH:2]=3)[CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 150751Trimethylsilylmethyl AzideHCID 86646759Methyl 3-ethynyl-5-(5-methylpyridin-2-yl)benzoate

Product 1

HCID 68496792Methyl 3-(5-methylpyridin-2-yl)-5-(1-((trimethylsilyl)methyl)-1H-1,2,3-triazol-5-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178424883HCID 178424883, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of methyl 3-ethynyl-5-(5-methylpyridin-2-yl)benzoate (124 mg, 0.493 mmol) in benzene (12 mL) were added trimethylsilylmethylazide (96 mg, 0.740 mmol) and pentamethylcyclopentadienylbis(triphenylphosphine)ruthenium(II) chloride (59 mg, 0.074 mmol) and the mixture heated to 80° C. in a sealed tube. After 16 h, the title compound was showed as the major isomer (10:1 isomeric ratio) in the reaction. The reaction was concentrated and purified by reverse-phase HPLC gave the title compound (120 mg). MS 381.1 (M+1).

Sources & evidence

ORD record
ord-61060f3b065749e49f49c687c3d63e84
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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