Methyl iodide → 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

HRID 877766Notes

Reaction equation

IC.[CH3:3][C:4]1([CH3:18])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=2)[O:5]1.[C:19](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:19][N:15]1[CH:16]=[C:11]([B:6]2[O:5][C:4]([CH3:18])([CH3:3])[C:8]([CH3:9])([CH3:10])[O:7]2)[CH:12]=[CH:13][C:14]1=[O:17]

Participants

Conditions

Temperature: 50 °C

Procedure

Iodomethane (0.283 mL, 4.52 mmol) was added to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (0.500 g, 2.262 mmol) and potassium carbonate (1.563 g, 11.31 mmol) in acetonitrile (10 mL). The reaction vial was sealed and stirred at 50° C. for 16 h. The resulting mixture was filtered to remove the inorganic salt and the filter cake rinsed with ethyl acetate. The filtrate was concentrated, treated with ethyl acetate (20 mL) and dichloromethane (20 mL), and filtered to remove the residual inorganic salt. The filtrate was concentrated and dried under vacuum to give crude 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one as white solid (399.4 mg). This material was used in subsequent Suzuki coupling reactions without further purification. 1H NMR (400 MHz, chloroform-d) δ ppm 7.76 (d, J=2.0 Hz, 1H), 7.60 (dd, J=9.2, 2.0 Hz, 1H), 6.52 (d, J=9.0 Hz, 1H), 3.55 (s, 3H), 1.31 (s, 12H).

Workup

customThe reaction
customvial was sealed
filtrationThe resulting mixture was filtered
customto remove the inorganic salt
washthe filter cake rinsed with ethyl acetate
concentrationThe filtrate was concentrated
additiontreated with ethyl acetate (20 mL) and dichloromethane (20 mL)
filtrationfiltered
customto remove the residual inorganic salt
concentrationThe filtrate was concentrated
customdried under vacuum

Sources & evidence

ORD record: ord-877459a48b2946cc94a339cabd6cf700
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987268B2

Reaction notes

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