Hydrogen Bromide → Ethyl 1-(2-oxo-2-(pyridin-3-yl)ethyl)-5-(trimethylsilyl)-1H-pyrazole-3-carboxylate

HRID 1409982Notes

Reaction equation

HRID 1409982 reaction equation
COC1C=CC(OC)=CC=1C(=O)CN1C(C(OCC)=O)=CC(C2C=NC=CC=2)=N1.[CH3:30][Si:31]([CH3:43])([CH3:42])[C:32]1[CH:36]=[C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[NH:34][N:33]=1.Br[CH2:45][C:46]([C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1)=[O:47].Br>>[O:47]=[C:46]([C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1)[CH2:45][N:33]1[C:32]([Si:31]([CH3:42])([CH3:43])[CH3:30])=[CH:36][C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N:34]1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 1514083-(2-Bromoacetyl)pyridineHCID 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 86267745Ethyl 1-(2-oxo-2-(pyridin-3-yl)ethyl)-5-(trimethylsilyl)-1H-pyrazole-3-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-(pyridin-3-yl)ethanone.HBr (purchased from Aldrich). 1H-NMR δ 9.17 (d, 1H), 8.88 (dd, 1H), 8.24 (ddd, 1H), 7.50 (td, 1H), 7.03 (s, 1H), 5.73 (s, 2H), 4.40 (q, 2H), 1.39 (t, 3H), 0.28 (s, 9H). Calculated mass for C16H21N3O3Si, 331.14, observed, 332.0 (M+1).

Sources & evidence

ORD record
ord-57bb5aff28c6446eae1dadfe7289b369
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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