Methanesulfonyl chloride → N-(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methanesulfonamide

HRID 1695728Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([NH:9][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (0.5 g, 1.999 mmol) in pyridine (5 ml) was added methanesulphonyl chloride (0.309 ml, 4.00 mmol) and the mixture stirred at 20° C. for 18 hr when the solvent was removed in vacuo. The residue was partitioned between saturated sodium bicarbonate solution (10 ml) and DCM (20 ml), separated by hydrophobic frit and purified by silica (70 g) cartridge on Flashmaster II using a gradient of DCM and methanol to give the title compound as a brown solid (0.46 g).

Workup

customwas removed in vacuo
customThe residue was partitioned between saturated sodium bicarbonate solution (10 ml) and DCM (20 ml)
customseparated by hydrophobic frit
custompurified by silica (70 g) cartridge on Flashmaster II

Sources & evidence

ORD record: ord-a5ce1c53fa034cf7b899d5d57b5df884
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

Loading…