1-Methyl-1H-1,2,3-triazole → HCID 118006037, compound

HRID 926529Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.CC#N.C(=O)=O.C([Li])CCC.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][N:21]=1>C1COCC1>[CH3:1][N:2]1[C:6]([CH:24]([C:23]2[CH:22]=[N:21][C:20]([C:19]([F:29])([F:18])[F:28])=[CH:27][CH:26]=2)[OH:25])=[CH:5][N:4]=[N:3]1

Participants

Conditions

Temperature: -40 °C

Procedure

A 50 mL flask containing 1-methyl-1H-1,2,3-triazole (0.47 g, 5.71 mmol) in dry THF (3 mL) was cooled to −43° C. (CH3CN—CO2 bath). n-Butyllithium (2.5 M in THF, 2.43 mL, 6.08 mmol) was then added dropwise resulting in a light blue suspension. The suspension was stirred at −40° C. for 40 minutes, and then a homogeneous solution of 6-(trifluoromethyl)nicotinaldehyde (1 g, 5.71 mmol) in THF (7 mL) was introduced at −40° C. The resulting homogeneous colorless solution was allowed to warm gradually to room temperature, and after 30 minutes, LC/MS showed that the reaction was complete. The mixture was quenched with water and aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide the title compound as a semi-solid which was carried on to the next step without further purification.

Workup

customresulting in a light blue suspension
temperatureto warm gradually to room temperature
waitafter 30 minutes
customThe mixture was quenched with water and aqueous NH4Cl
extractionextracted with EtOAc (2×)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-524f4288b06248e48b762605c891df95
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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