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

HRID 885939Notes

Reaction equation

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

Participants

Reactant 2

HCID 8471Triethylamine

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 57722832N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine

Conditions

Temperature: 90 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 2-chloro-N,N-(dimethyl)ethylamine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 2-chloro-N,N-(dimethyl)ethylamine hydrochloride and triethylamine, then heating to 90° C. for a further 3 days) and was isolated as a brown oil (43%). LCMS (ES+) 266 (M+H)+, RT 1.73 minutes (Method 1).

Sources & evidence

ORD record: ord-e7ece009a9574f82a76ecba77e0b76db
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242116B2

Reaction notes

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