Phenethyl bromide → HCID 70929327, compound

HRID 531450Notes

Reaction equation

HRID 531450 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[H-].[Na+].[CH2:17](Br)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:17]([N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 70929327HCID 70929327, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (300 mg, 1.5463 mmol) in DMF (2 ml) cooled at 0° C. was added sodium hydride (124 mg, 3.0927 mmol) and stirred at 0° C. for further 20 min. Phenethyl bromide (344 mg, 1.8556 mmol) was then added drop wise and stirred the reaction at RT for 3 hrs. The reaction mixture was diluted with ice water (150 ml) and extracted with dichloromethane (2×50 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 300 mg (43.47% yield) of the titled compound. MS: m/z=299.4 (M+1). 1H NMR (CDCl3, 300 MHz): δ 7.81 (s, 1H), 7.54 (s, 1H), 7.29-7.21 (m, 2H), 7.10-7.08 (d, 1H), 4.35-4.30 (t, 2H), 3.19-3.14 (t, 2H), 1.28 (s, 12H).

Workup

  1. stirringstirred
  2. customthe reaction at RT for 3 hrs
  3. extractionextracted with dichloromethane (2×50 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fa72959385f4950ac15011742fad442
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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