1-(2-Chloroethyl)pyrrolidine hydrochloride → 1-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 885938Notes

Reaction equation

HRID 885938 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][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[N:19]1([CH2:18][CH2:17][N:2]2[CH:3]=[C:4]([B:6]3[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:13])([CH3:12])[O:14]3)[CH:5]=[N:1]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2×HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 588858611-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions

Temperature
90 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 1-(2-chloroethyl)pyrrolidine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 1-(2-chloroethyl)pyrrolidine hydrochloride, and heating to 90° C. for a further 3 days) and was isolated as a brown gum (45%). LCMS (ES+) 292 (M+H)+, RT 1.81 minutes (Method 1).

Sources & evidence

ORD record
ord-0ae0a80ff3494422a8949cd746358b05
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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