5-(Chloromethyl)-1,2,3-trimethoxybenzene → Ethyl 1-(3,4,5-trimethoxybenzyl)-3-(trimethylsilyl)-1H-pyrazole-5-carboxylate

HRID 1409980Notes

Reaction equation

HRID 1409980 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.[CH3:44][O:45][C:46]1[CH:47]=[C:48]([CH:51]=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[CH2:49]Cl>>[CH3:57][O:56][C:52]1[CH:51]=[C:48]([CH:47]=[C:46]([O:45][CH3:44])[C:53]=1[O:54][CH3:55])[CH2:49][N:34]1[C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:36][C:32]([Si:31]([CH3:42])([CH3:43])[CH3:30])=[N:33]1

Participants

4

Reactant 3

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 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 86267743Ethyl 1-(3,4,5-trimethoxybenzyl)-3-(trimethylsilyl)-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 3,4,5-trimethoxy benzyl chloride (purchased from Aldrich). 1H-NMR δ 6.98 (s, 1H), 6.21 (s, 2H), 5.44 (s, 2H), 4.41 (q, 2H), 3.81 (s, 3H), 3.76 (s, 6H), 1.40 (t, 3H), 0.22 (s, 9). Calculated mass for C19H28N2O5Si, 392.18, observed, 393.0 (M+1), 415.1 (M+Na).

Sources & evidence

ORD record
ord-8ae9ffc3117742dfa22ce29c5930932f
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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