Potassium Carbonate → HCID 25154364, compound

HRID 1517522Notes

Reaction equation

HRID 1517522 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[CH3:14][N:15]1[C:19]([CH3:20])=[C:18](B2OC(C)(C)C(C)(C)O2)[C:17]([CH3:30])=[N:16]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O>[CH3:12][N:11]([CH3:13])[CH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:18]3[C:17]([CH3:30])=[N:16][N:15]([CH3:14])[C:19]=3[CH3:20])[CH:10]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 22349540HCID 22349540, compound

Product 1

HCID 25154364HCID 25154364, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

(Method 3): (6-Bromo-indan-1-yl)-dimethyl-amine (0.82 mmol) was dissolved in DME/H2O 1/1 (10 mL) under argon atmosphere. 1,3,5-Trimethyl-1H-pyrazole-4-boronic acid pinacol ester (0.82 mmol), K2CO3 (3.08 mmol), and tetrakis-(triphenylphosphine)palladium (3 mol %, 0.025 mmol) were added and the reaction mixture was stirred at 100° C. for 3 h. Then, a second fraction of 1,3,5-trimethyl-1H-pyrazole-4-boronic acid pinacol ester (0.41 mmol) was added and the reaction mixture was stirred at 100° C. for 2 h more. The reaction mixture was evaporated to dryness, then dissolved in CHCl3 and filtered through Celite® to give the crude product dimethyl-[6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-indan-1-yl]-amine. The crude was purified by flash column chromatography (CH2Cl2 and MeOH as eluents) by using a CombiFlash Companion™ system to yield the base of the title compound. The obtained product was diluted in ethyl acetate and a solution of hydrogen chloride 2.0 M in diethylether was added. The resulting precipitate was filtered and dried under vacuum to yield the title compound dimethyl-[6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-indan-1-yl]-amine dihydrochloride (75%). MS [MH]+=270.

Workup

  1. stirringthe reaction mixture was stirred at 100° C. for 2 h more
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutiondissolved in CHCl3
  4. filtrationfiltered through Celite®

Sources & evidence

ORD record
ord-4dddb7c198364906a68391bf7a346bcb
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

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