Acetic Acid → 3-Fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 468933Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:4][N:3]=1.C(O)(=O)C>C(OCC)(=O)C.[Zn]>[F:8][C:7]1[CH:2]=[N:3][CH:4]=[C:5]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[C:6]=1[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-chloro-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (212 mg; 0.7808 mmol), zinc powder (155.3 mg; 2.37 mmol), and acetic acid (3.0 mL; 47 mmol) was heated at 60° C. for 3 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate (30 mL) filtered through celite, and evaporated under vacuum to yield the title compound in quantitative yield. LCMS (ESI): [M-pinacol]+H=156.4; 1H NMR (400 MHz, DMSO) δ 8.55-8.47 (m, 2H), 2.42 (d, J=2.0 Hz, 3H), 1.33 (s, 12H).

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through celite
customevaporated under vacuum

Sources & evidence

ORD record: ord-3ca3c0bb03ab475b9248b2396a863fda
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623889B2

Reaction notes

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