Dimethylamine → N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine

HRID 2427524Notes

Reaction equation

HRID 2427524 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1.C1COCC1.[I-].[K+].[CH3:25][NH:26][CH3:27]>O>[CH3:25][N:26]([CH3:27])[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 4875Potassium IodideHCID 8028TetrahydrofuranHCID 579497411-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 57722832N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Chloro-ethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (664 mg, 2.59 mmol) was dissolved in a 2M solution of dimethyl amine in THF (15.32 mL, 30.6 mmol) and stirred for 48 hrs at room temperature. A scoop of potassium iodide was added to the reaction flask and the mixture stirred at 75° C. for 48 hrs. The mixture was cooled, diluted with water and extracted with ethyl acetate. The organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (519 mg, 76%). 1H NMR (300 MHz, CDCl3): δ 7.79 (d, 2H), 4.35 (t, 2H), 2.95 (t, 2H), 2.37 (s, 6H), 1.32 (s, 12H).

Workup

  1. stirringthe mixture stirred at 75° C. for 48 hrs
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ad6aec489dfb4e78b1e9c795a989bb18
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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