Potassium Iodide → N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine

HRID 1530446Notes

Reaction equation

HRID 1530446 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+].Br[CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[I-].[K+]>O1CCCC1.C(OCC)(=O)C.O>[CH2:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH2:22][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)[CH3:18]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 706082-Bromo-N,N-diethylethanamineHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 58204670N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamineYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,4,5,5-tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (250 mg, 1.29 mmol) and sodium hydride (61.8 mg, 2.58 mmol) in tetrahydrofuran at 0° C. was added 2-bromo-N,N-diethylethanamine (558 mg, 2.58 mmol). The reaction was allowed to warm up to room temperature and was monitored by LCMS. After 90 minutes there was still no reaction and potassium iodide (1.71 g, 10.3 mmol) was added and the reaction was heated at 50° C. overnight. The reaction mixture was diluted with a large volume of ethyl acetate and water and partitioned. The organic layer containing the product was washed with brine and concentrated in vacuo to give clear thick oil confirmed by LCMS to be 100% pure N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine (340 mg, yield 90%, M+1 294.2)

Workup

  1. additionwas added
  2. temperaturethe reaction was heated at 50° C. overnight
  3. custompartitioned
  4. additionThe organic layer containing the product
  5. washwas washed with brine
  6. concentrationconcentrated in vacuo
  7. customto give clear thick oil

Sources & evidence

ORD record
ord-f5f04272c9d648f68cf6fed9f683f607
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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