2-Bromo-1-(2,4-dimethoxyphenyl)ethanone → Ethyl 1-(2-(2,4-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxylate

HRID 1409981Notes

Reaction equation

HRID 1409981 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](OC)=[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:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:14]1.N1C=CC=C(C2C=C([C:41](OCC)=[O:42])NN=2)C=1.BrCC(C1C=CC(OC)=CC=1OC)=O>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:42][CH3:41])[CH:6]=[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:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:14]1

Participants

4

Reactant 3

HCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanoneHCID 575603Ethyl 3-(pyridin-3-yl)-1H-pyrazole-5-carboxylateHCID 86267540Ethyl 1-(2-(2,5-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-3-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 86267744Ethyl 1-(2-(2,4-dimethoxyphenyl)-2-oxoethyl)-3-(pyridin-3-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-(pyridin-3-yl)-1H-pyrazole-5-carboxylate and 2-bromo-1-(2,4-dimethoxyphenyl)ethanone (purchased from Aldrich). 1H-NMR δ 9.08 (s, 1H), 8.58 (d, 1H), 8.14 (d, 1H), 8.00 (d, 1H), 7.33 (m, 11-1), 7.27 (s, 1H), 6.58 (dd, 1H), 6.49 (d, 1H), 5.98 (s, 2H), 4.31 (q, 2H), 4.00, (s, 3H), 3.88 (s, 3H), 1.34 (t, 3H). Calculated mass for C21H21N3O5, 395.15, observed, 396.2 (M+1).

Sources & evidence

ORD record
ord-1ce070313d314c3b9f6d41b63d699411
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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