Dimethylformamide → 1-Cyclohex-2-enyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

HRID 595185Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Br[CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>C(OCC)C>[CH:21]1([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (250 mg, 1.29 mmol), 3-bromocyclohexene (0.17 mL, 1.42 mmol), and cesium carbonate (462 mg, 1.42 mmol) were added to an oven-dried flask, followed by DMF (4.3 mL). The reaction mixture was stirred at 90° C. overnight then cooled to room temperature, diluted with diethyl ether, washed with water (3×50 mL) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 1-(cyclohex-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. 1H NMR (500 MHz, CD3OD) δ 7.82 (s, 1H), 7.69 (s, 1H), 5.81-5.62 (m, 2H), 4.15-4.09 (m, 1H), 2.24-1.41 (m, 6H), 1.31 (s, 12H).

Workup

temperaturethen cooled to room temperature
washwashed with water (3×50 mL) and brine
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-486788854b5e480b9360e1772c3fe447
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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