Potassium Carbonate → 1-(3-Fluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

HRID 531437Notes

Reaction equation

HRID 531437 reaction equation
[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[C:5]([CH3:16])[NH:4][N:3]=1.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][N:3]1[C:2]([CH3:1])=[C:6]([B:7]2[O:11][C:10]([CH3:12])([CH3:13])[C:9]([CH3:15])([CH3:14])[O:8]2)[C:5]([CH3:16])=[N:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol ester

Product 1

HCID 900306711-(3-Fluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazoleYield 94.59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using similar reaction conditions as described in (step i of Intermediate-2), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 g, 4.5 mmol) was reacted with 3-fluoro benzyl bromide (1.02 g, 5.4 mmol) in DMF (10 ml) and potassium carbonate (1.86 g, 13.5 mmol) to afford 1.4 g (94.59% yield) of the pure product.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4ce1b45cddd44f05b9b6b7f5e518dd19
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…