Chloride → HCID 77231543, compound

HRID 882182Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl-]>ClCCl>[CH3:12][C:10]1([CH3:11])[C:13]([CH3:15])([CH3:14])[O:16][B:8]([C:4]2[CH:3]=[C:2]([NH:1][C:10](=[O:9])[C:13]([CH3:15])=[CH2:14])[CH:7]=[CH:6][CH:5]=2)[O:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-aminophenylboronic acid pinacol ester (5.04 g, 23.0 mmol) in dichloromethane (100 mL) was added TEA (6.41 mL, 46.0 mmol). The resulting solution was cooled to 0° C., then methacrolyl chloride (2.70 mL, 27.6 mmol) was added. The cooling bath was removed, and the reaction was allowed to warm to room temperature and stir for approximately 2 hours. The reaction mixture was washed with 7.5% aqueous ammonium chloride (100 mL) and the layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford a solid. The solid was triturated with hexanes (50 mL) and isolated by filtration to afford N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methacrylamide. LRMS (ESI) calcd for C16H22BNO3 [M+H]+: 288, found 288.

Workup

customThe cooling bath was removed
temperatureto warm to room temperature
washThe reaction mixture was washed with 7.5% aqueous ammonium chloride (100 mL)
customthe layers were separated
dry with materialthe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto afford a solid
customThe solid was triturated with hexanes (50 mL)
customisolated by filtration

Sources & evidence

ORD record: ord-5dcecb9fab5246f6b2f093d3d6c2e4f2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993756B2

Reaction notes

Loading…