4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 1-methyl-2-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}-piperidine

HRID 885941Notes

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.Cl.Cl[CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[CH3:25]>C(N(CC)CC)C>[CH3:25][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[CH2:18][CH2:17][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

Conditions

Temperature: 90 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 2-(2-chloroethyl)-1-methylpiperidine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 2-(2-chloroethyl)-1-methylpiperidine hydrochloride and triethylamine, then heating to 90° C. for a further 3 days) and was isolated as a brown oil (quantitative). LCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1).

Workup

customwas isolated as a brown oil (quantitative)
customLCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1)

Sources & evidence

ORD record: ord-12b5f441e4c44dbdbd08311f4b240217
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242116B2

Reaction notes

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