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

HRID 631926Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

In a 250 mL round-bottomed flask, 5-(4-bromo-2-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (291 mg, 887 μmol) was combined with tetrahydrofuran (18 mL) to give a colorless solution. 1M LiOH (9 mL, 9.00 mmol, Eq: 10.1) was added and the reaction was stirred at 25° C. for 15 h. The crude reaction mixture was concentrated in vacuo and acidified with 10 mL of 1M HCl. The reaction was diluted with EtOAc and the organic layer was washed with H2O (1×20 mL) and saturated NaCl (1×20 mL), dried over Na2SO4 and concentrated in vacuo. The white powder was dried under vacuum to afford 266 mg (100%) of the desired product. (M−H)−=297.8 and 299.9 (m/e).

Workup

customto give a colorless solution
customThe crude reaction mixture
concentrationwas concentrated in vacuo
additionThe reaction was diluted with EtOAc
washthe organic layer was washed with H2O (1×20 mL) and saturated NaCl (1×20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe white powder was dried under vacuum

Sources & evidence

ORD record: ord-4c69b782ffbe4556a6f33622fc3b673d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321738B2

Reaction notes

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