2-Bromo-2',5'-dimethoxyacetophenone → Ethyl 1-(2-(2,5-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-2-yl)-1H-pyrazole-5-carboxylate

HRID 1409984Notes

Reaction equation

HRID 1409984 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH2:12][N:13]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15](C2C=NC=CC=2)=[N:14]1.C[Si](C)(C)[C:32]1[CH:36]=[C:35]([C:37](OCC)=O)N[N:33]=1.Br[CH2:45]C(C1C=C(OC)C=CC=1OC)=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH2:12][N:13]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][C:15]([C:45]2[CH:37]=[CH:35][CH:36]=[CH:32][N:33]=2)=[N:14]1

Participants

4

Reactant 3

HCID 709972-Bromo-2',5'-dimethoxyacetophenoneHCID 86267540Ethyl 1-(2-(2,5-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxylateHCID 178469409Ethyl 3-(trimethylsilyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 86267747Ethyl 1-(2-(2,5-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-2-yl)-1H-pyrazole-5-carboxylate

Procedure

This compound was made in an analogous fashion to ethyl 1-(2-(2,5-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxylate using ethyl 3-(trimethylsilyl)-1H-pyrazole-5-carboxylate and 2-bromo-1-(2,5-dimethoxyphenyl)ethanone (purchased from Aldrich). 1H-NMR δ 8.65 (dt, 1H), 7.94 (d, 1H), 7.72 (dd, 1H), 7.57 (s, 1H), 7.47 (d, 1H), 7.22 (dd, 1H), 7.13 (dd, 1H), 6.98 (s, 1H), 6.05 (s, 2H), 4.28 (q, 2H), 3.98 (s, 3H), 3.78 (s, 3H), 1.33 (t, 3H). Calculated mass for C21H21N3O5, 395.15, observed, 396.2 (M+1).

Sources & evidence

ORD record
ord-cedc36a119bf43879fdf8846208c159c
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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