3-Chloro-1-propanol → 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol

HRID 885936Notes

Reaction equation

HRID 885936 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[CH2:16][CH2:17][CH2:18][OH:19]>C(N(CC)CC)C>[CH3:12][C:11]1([CH3:13])[C:8]([CH3:9])([CH3:10])[O:7][B:6]([C:4]2[CH:3]=[N:2][N:1]([CH2:16][CH2:17][CH2:18][OH:19])[CH:5]=2)[O:14]1

Participants

4

Reactant 2

HCID 123133-Chloro-1-propanol2×HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 671871273-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 3-chloro-1-propanol according to Method AC (heating to 90° C. for 6 days before addition of further 3-chloro-1-propanol and triethylamine, and heating to 90° C. for a further 3 days) and was isolated as a brown gum (quantitative). LCMS (ES+) 253 (M+H)+, RT 2.53 minutes (Method 1).

Workup

  1. customwas isolated as a brown gum (quantitative)
  2. customLCMS (ES+) 253 (M+H)+, RT 2.53 minutes (Method 1)

Sources & evidence

ORD record
ord-41401df9190a42388ddb636c5410bcab
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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