Tetrabutylammonium Fluoride → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol

HRID 876410Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro-8-(triisopropylsilyloxy)quinoline (5.00 g, 11.5 mmol) was dissolved in 250 mL of anhydrous THF, followed by cooling to 0° C., then addition of TBAF (4.49 g, 17.2 mmol). Following 1 hour, the reaction was complete by TLC, and the crude reaction partitioned between water and ethyl acetate. The crude work-up was then filtered through standard filter paper with ethyl acetate wash, affording the desired product 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol (2.8 g, 9.99 mmol, 87% yield) as a white solid.

Workup

customthe crude reaction
custompartitioned between water and ethyl acetate
filtrationThe crude work-up was then filtered through standard filter paper with ethyl acetate
washwash

Sources & evidence

ORD record: ord-cbb1654dbff048e3873519867302eb71
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987251B2

Reaction notes

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