1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 25234413, compound

HRID 1675515Notes

Reaction equation

HRID 1675515 reaction equation
Br[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]=1[CH3:8].[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1>>[CH3:8][C:3]1[C:4](=[O:7])[CH2:5][CH2:6][C:2]=1[C:13]1[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 112982573-bromo-2-methylcyclopent-2-enone

Product 1

HCID 25234413HCID 25234413, compoundYield 16%

Procedure

Synthesized from 3-bromo-2-methylcyclopent-2-enone and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 100% ethyl acetate/hexanes) and further recrystallization yielded the product (21 mg, 16%) as a white solid. 1H NMR (CDCl3, 300 MHz): δ 7.80 (s, 1H), 7.70 (s, 1H), 2.84-2.80 (m, 2H), 2.52-2.48 (m, 2H), 1.95 (t, J=2.1 Hz, 3H). LCMS (ESI): mass calcd for (C10H12N2O) m/z 176.09; measured [M+H]+: m/z 177.09.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 100% ethyl acetate/hexanes) and further recrystallization

Sources & evidence

ORD record
ord-05b7a6bfaef14df28f80765a556bf009
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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