(6-Methoxypyridin-3-yl)boronic acid → HCID 24894068, compound

HRID 1675508Notes

Reaction equation

HRID 1675508 reaction equation
Br[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH3:8].[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1>>[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:2]2[CH2:6][CH2:5][C:4](=[O:7])[C:3]=2[CH3:8])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 112982573-bromo-2-methylcyclopent-2-enone

Product 1

HCID 24894068HCID 24894068, compoundYield 92%

Procedure

Synthesized from 3-bromo-2-methylcyclopent-2-enone and 6-methoxypyridine-3-boronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography yielded the product (138 mg, 92%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 8.41 (d, J=2.2 Hz, 1H), 7.77 (dd, J=8.5, 2.5 Hz, 1H), 6.83 (d, J=8.5 Hz, 1H), 3.99 (s, 3H), 2.92-2.87 (m, 2H), 2.56-2.53 (m, 2H), 1.99 (t, J=1.9 Hz, 3H). 13C (75 MHz, CDCl3): δ 208.9, 164.4, 162.6, 146.4, 137.4, 135.9, 125.4, 110.9, 53.8, 33.8, 28.7, 10.2. LCMS (ESI): mass calcd for (C12H13NO2) m/z 203.09; measured [M+H]+: m/z 204.09.

Workup

  1. customPurification by automated flash chromatography

Sources & evidence

ORD record
ord-ed3941ef9c2d4fde8060d14be962b8b3
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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