Methyl iodide → 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2090393Notes

Reaction equation

HRID 2090393 reaction equation
[CH3:1]C(C)([O-])C.[K+].C1COCC1.[CH3:12][C:13]1([CH3:25])[C:17]([CH3:19])([CH3:18])[O:16][B:15]([C:20]2[CH:24]=[CH:23][NH:22][N:21]=2)[O:14]1.CI>CN(C=O)C.C(OCC)(=O)C>[CH3:1][N:22]1[CH:23]=[CH:24][C:20]([B:15]2[O:16][C:17]([CH3:18])([CH3:19])[C:13]([CH3:25])([CH3:12])[O:14]2)=[N:21]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178431094HCID 178431094, compound

Product 1

HCID 27600771-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide in THF (1.0 M, 0.309 mL, 0.309 mmol) was added to a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (30.0 mg, 0.155 mmol, Alfa Aesar, Cat. No. H27619) in DMF (0.5 mL) and stirred at r.t. for 10 min, and then methyl iodide (28.9 uL, 0.464 mmol) was added and the stirred at r.t. for 1 h. LCMS showed the reaction was complete. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated to give the crude product which was directly used in the next reaction without further purification. LCMS (M+H−82)+: m/z=127.2.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c621b4d8a104c539f4274238cf8127d
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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