Potassium Carbonate → tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate

HRID 521617Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH:3]=1.Br[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][CH:10]=2)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol (3.02 g, 15.96 mmol), tert-butyl 2-bromoethylcarbamate (7.153 g, 2.0 eq) and potassium carbonate (4.412 g, 2.0 eq) were dissolved in 100 mL acetone and refluxed at 60° C. for 24 h. After reaction, the potassium carbonate was filtered and acetone was evaporated. The residue was dissolved in 100 mL DCM and extracted with 3×100 mL 1N NaOH. Purified by column chromatography (50-100% ethyl acetate in hexane) to afford the title compound as a yellow oil in 29.10% yield. LCMS m/z (%)=333 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 1.43 (s, 9H), 3.33 (q, J=5.05 Hz, 2H), 3.75 (s, 3H), 3.91 (t, J=5.05 Hz, 2H), 4.45-4.51 (m, 1H), 6.23 (d, J=2.02 Hz, 1H), 6.62 (d, J=3.03 Hz, 1H), 6.73 (dd, J=8.59, 3.03 Hz, 1H), 6.85 (d, 1H), 7.52 (d, J=2.02 Hz, 1H).

Workup

customAfter reaction
filtrationthe potassium carbonate was filtered
customacetone was evaporated
dissolutionThe residue was dissolved in 100 mL DCM
extractionextracted with 3×100 mL 1N NaOH
customPurified by column chromatography (50-100% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-a6b9a629aa254d099c4c9d1fcf9de4ea
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328107B2

Reaction notes

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