Cesium carbonate → N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine

HRID 1052255Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (60.0 mg, 0.309 mmol), β-dimethylaminoethyl chloride hydrochloride (49.0 mg, 0.340 mmol) and cesium carbonate (0.302 g, 0.928 mmol) in acetonitrile (1 mL) was stirred at 90° C. overnight. The reaction mixture was cooled to ambient temperature, quenched with water, and extracted with methylene chloride. The combined organic layers were dried over MgSO4, then filtered and concentrated under reduced pressure to give the desired product (60 mg, 88%). LCMS calculated for C13H25BN3O2 (M+H)+: m/z=266.2. Found: 266.2.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customquenched with water
extractionextracted with methylene chloride
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4313058b79b9456d8ee79888b34eed98
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388185B2

Reaction notes

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