Potassium Carbonate → 2-(3-((4-Bromo-1H-pyrazol-1-yl)methyl)phenoxy)ethyl acetate

HRID 2175288Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH:6]=1.[C:15]([O:18][CH2:19][CH2:20]Br)(=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:15]([O:18][CH2:19][CH2:20][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:5]2[CH:6]=[C:2]([Br:1])[CH:3]=[N:4]2)[CH:9]=1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 3-((4-bromo-1H-pyrazol-1-yl)methyl)phenol (0.6 g, 2.37 mmol), 2-bromoethyl acetate (0.792 g, 4.74 mmol) and potassium carbonate (0.655 g, 4.74 mmol) in DMF (5 mL) was heated at 200° C. in a microwave reactor for 1 h. After this time, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.27 g, 34% yield) as a colorless oil. LCMS, [M+H]+=339.0. 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.34 (s, 1H), 7.24 (dd, J=8.3, 7.6 Hz, 2H), 6.83 (dd, J=8.3, 2.4 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.74 (d, J=2.4 Hz, 1H), 5.20 (s, 2H), 4.41-4.32 (m, 2H), 4.14-4.08 (m, 2H), 2.06 (s, 3H).

Workup

customAfter this time, the reaction mixture was quenched with water
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-ca5dc099bc244b0b8a59fb1957e7d919
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062028B2

Reaction notes

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