Hydrochloric Acid → (6-Methoxypyridin-3-yl)boronic acid

HRID 1913357Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Li]CCCC.[B:15](OC(C)C)([O:20]C(C)C)[O:16]C(C)C.Cl>>[B:15]([OH:20])([OH:16])[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 21531Triisopropyl borate

HCID 27348955-Bromo-2-methoxypyridine

HCID 178418339Butyllithium

Product 1

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidYield 89%

Procedure

5-Bromo-2-methoxypyridine (5.0 mL, 39.1 mmol) was treated with n-BuLi (1.6 M in hexanes, 26.9 mL, 43.0 mmol), triisopropyl borate (10.8 mL, 46.9 mmol) and HCl(aq) (2.7 N, 37.6 mL) as for 1 to give the title compound 3 (4.3 g, 89% yield) as a white solid: 1H NMR (CD3OD) δ 8.42 (m, 1H), 7.95 (br s, 1H), 6.76 (br s, 1H), 3.91 (s, 3H). This material was used directly in Suzuki cross coupling reactions.

Sources & evidence

ORD record: ord-2d60579449424923bf47ca19538a9590
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609708B2

Reaction notes

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