Potassium Carbonate → HCID 58173147, compound

HRID 1517519Notes

Reaction equation

HRID 1517519 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:12][N:13]1[C:17]([CH3:18])=[C:16](B2OC(C)(C)C(C)(C)O2)[C:15]([CH3:28])=[N:14]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O>[CH3:12][N:13]1[C:17]([CH3:18])=[C:16]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[C:15]([CH3:28])=[N:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1397781-Indanone, 6-bromo-HCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 58173147HCID 58173147, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-indan-1-one (0.94 mmol) was dissolved in DME/H2O 1/1 (10 mL) under argon atmosphere. 1,3,5-Trimethyl-1H-pyrazole-4-boronic acid pinacol ester (1.42 mmol), K2CO3 (2.82 mmol), and tetrakis-(triphenylphosphine)palladium (5 mol %, 0.047 mmol) were added and the reaction mixture was stirred at 100° C. for 3 h. The reaction mixture was evaporated to dryness, then dissolved in CHCl3 and filtered through Celite® to give the crude product 6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-indan-1-one. The crude was purified by flash column chromatography (AcOEt-Cyclohexane as eluents) by using a CombiFlash Companion™ system to yield the title compound (84%). MS [MH]+=240

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in CHCl3
  3. filtrationfiltered through Celite®

Sources & evidence

ORD record
ord-e4eabe18a5ab4f53a213b5945e9a6b2f
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

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