Lithium Hydroxide → 1-(4-Bromo-6-fluoro-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid

HRID 538190Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]([F:21])[CH:18]=[C:19]([Br:20])[C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.[Li+].[OH-].C1COCC1>O>[Br:20][C:19]1[C:13]2[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)[NH:15][C:14]=2[CH:16]=[C:17]([F:21])[CH:18]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 1-(4-bromo-6-fluoro-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (16.0 mg, 45.0 mmol), LiOH (10.0 mg, 0.230 mmol), THF (0.5 mL), and H2O (0.17 mL) was stirred at 23° C. for 16 h. THF was removed under reduced pressure and then aqueous HCl was added. The resulting precipitate was collected and washed with water to yield the titled compound (10.0 mg, 67%). MS (ESI/CI): mass calcd. for C11H6BrFN4O2, 325.1; m/z found, 326.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.82 (s, 1H), 12.94 (s, 1H), 8.87 (s, 1H), 8.30 (d, J=0.5 Hz, 1H), 7.45 (dd, J=9.6, 2.3 Hz, 1H), 7.32 (s, 1H).

Workup

customTHF was removed under reduced pressure
additionaqueous HCl was added
customThe resulting precipitate was collected
washwashed with water

Sources & evidence

ORD record: ord-329c690ac7cd4178909ccf1e255240d2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865713B2

Reaction notes

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