4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 89924537, compound

HRID 1505673Notes

Reaction equation

HRID 1505673 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[NH:10]1[CH:14]=[C:13]([B:15]2[O:23][C:20]([CH3:22])([CH3:21])[C:17]([CH3:19])([CH3:18])[O:16]2)[CH:12]=[N:11]1>C(#N)C>[N:5]1([C:3](=[O:4])[CH2:2][N:11]2[CH:12]=[C:13]([B:15]3[O:16][C:17]([CH3:19])([CH3:18])[C:20]([CH3:22])([CH3:21])[O:23]3)[CH:14]=[N:10]2)[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 111061881-(Bromoacetyl)pyrrolidine

Product 1

HCID 89924537HCID 89924537, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1-(bromoacetyl)pyrrolidine (Chemical Diversity Labs; 3.0 g, 15.6 mmol, 1.2 eq.) in acetonitrile (15 mL) was slowly added over a suspension of pyrazole-4-boronic acid pinacol ester (2.5 g, 12.9 mmol, 1 eq.) in acetonitrile and stirred overnight at RT. The reaction mixture was filtered and the filtrate was diluted with DCM and washed with water then brine. Separated organic phase was dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow oil (2.72 g, 100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with DCM
  3. washwashed with water
  4. dry with materialSeparated organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd879811ab904a9d8d3b6a8342da3428
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

Loading…