Water → 5-(4-bromo-2-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 631925Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][Si](C)(C)C)[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=1[F:18])=[O:5])[CH3:2].O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:19])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=1[F:18])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 250 mL round-bottomed flask, 5-(4-bromo-2-fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (616 mg, 1.54 mmol) and water (55.4 mg, 55.4 μL, 3.08 mmol, Eq: 2) were combined with tetrahydrofuran (13 mL) to give a light yellow solution. The reaction was cooled to 0° C. and 1M TBAF in THF (1.85 ml, 1.85 mmol, Eq: 1.2) was added. The reaction was stirred for 20 mins at 0° C. then concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 20% EtOAc in heptane) to afford 291 mg (58%) of the desired product as a white solid. (M+H)+=327.9/329.9 m/e; 1H NMR (DMSO-d6) δ ppm 7.73 (dq, J=9.9, 0.7 Hz, 1H), 7.50-7.62 (m, 2H), 4.29 (s, 3H), 4.25 (q, J=7.1 Hz, 2H), 1.14 (t, J=7.1 Hz, 3H).

Workup

customto give a light yellow solution
concentrationthen concentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 40 g, 0% to 20% EtOAc in heptane)

Sources & evidence

ORD record: ord-598e0acbbb0748faaf2821453e7677c8
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321738B2

Reaction notes

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