Cesium carbonate → HCID 123962438, compound

HRID 595204Notes

Reaction equation

Br[CH2:2][C:3]([CH3:7])=[C:4]([CH3:6])[CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:14][C:15]1([CH3:27])[C:19]([CH3:21])([CH3:20])[O:18][B:17]([C:22]2[CH:23]=[N:24][NH:25][CH:26]=2)[O:16]1>CN(C=O)C.C(OCC)C>[CH3:7][C:3](=[C:4]([CH3:6])[CH3:5])[CH2:2][N:25]1[CH:26]=[C:22]([B:17]2[O:16][C:15]([CH3:27])([CH3:14])[C:19]([CH3:21])([CH3:20])[O:18]2)[CH:23]=[N:24]1

Participants

Conditions

Temperature: 90 °C

Procedure

1-Bromo-2,3-dimethylbut-2-ene (3.78 g, 23.19 mmol), and cesium carbonate (15.11 g, 46.4 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3.0 g, 15.46 mmol) in DMF (52 mL), and the mixture was stirred at 90° C. for 18 h. The mixture was allowed to cool to room temperature, diluted with diethyl ether, washed with water (3×50 mL) and brine. The organic layers were separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-40% EtOAc/hexane) to afford 1-(2,3-dimethylbut-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. 1H NMR (500 MHz, CDCl3) δ 7.79 (s, 1H), 7.62 (s, 1H), 4.74 (s, 2H), 1.83 (s, 3H), 1.74 (s, 3H), 1.59 (s, 3H), 1.31 (s, 12H).

Workup

temperatureto cool to room temperature
washwashed with water (3×50 mL) and brine
customThe organic layers were separated
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0-40% EtOAc/hexane)

Sources & evidence

ORD record: ord-968228ede5e7435aa03eafd70416b347
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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