Methanesulfonyl chloride → HCID 86685293, compound

HRID 1852946Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH2:14][CH2:15][OH:16])[CH:13]=2)[O:3]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:16][CH2:15][CH2:14][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:17])([CH3:1])[O:3]2)[CH:10]=[N:11]1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol (0.150 g, 0.630 mmol) and TEA (0.132 mL, 0.945 mmol) in 5 mL of DCM was added methansulfonyl chloride (0.0536 mL, 0.693 mmol) with stirring at 0° C. The reaction was allowed to proceed at 0° C. for 30 minutes. The reaction was loaded directly onto a silica gel column pre-pre-wetted with and eluted with 50% ethyl acetate in hexanes to afford 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate (0.169 g, 0.513 mmol, 81.4% yield) MS (apci) m/z=317.1 (M+H).

Workup

washeluted with 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-d686063139934cb08362cd1eb209eeb8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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