ChemicalBook CAS DataBase List Ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate

Ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate synthesis

5synthesis methods

Product Name:Ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate
CAS Number:1355249-29-4
Molecular formula:C14H15IN2O3
Molecular Weight:386.18

179692-08-1

824-94-2

Ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate

1355249-29-4

To a solution of ethyl 4-iodo-1H-pyrazole-3-carboxylate (38 g, 143 mmol) in acetonitrile (380 mL) was added potassium carbonate (39.5 g, 286 mmol) followed by 1-(chloromethyl)-4-methoxybenzene (24 mL, 177 mmol) at room temperature. The reaction mixture was stirred at 60 °C overnight. After completion of the reaction, the mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazole-3-carboxylate (32 g, 58% yield). The compound was characterized by proton nuclear magnetic resonance (1H NMR) and mass spectrometry (MS). 1H NMR (DMSO-d6, 400 MHz) data were as follows: δ 8.13 (s, 1H), 7.23 (d, J = 8.8 Hz, 2H), 6.90 (d, J = 8.8 Hz, 2H), 5.29 (s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H), 1.26 (t, J = 6.8 Hz, 3H). Mass spectrometry (ESI) showed the molecular ion peak m/z 387 ([M + H]+).

179692-08-1
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$13.00/250mg

824-94-2 Synthesis

824-94-2
445 suppliers
$24.19/5G

1355249-29-4
26 suppliers
$65.00/100mg

Yield:1355249-29-4 58%

Reaction Conditions:

with potassium carbonate in acetonitrile at 60;

Steps:

15.C

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K₂C0₃ (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60°C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (¹HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: ¹H NMR (DMSO-d6, 400MHz): δ 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)⁺.

References:

WO2012/6760,2012,A1 Location in patent:Page/Page column 47-48

179692-08-1
73 suppliers
$13.00/250mg

824-94-2 Synthesis

824-94-2
445 suppliers
$24.19/5G

1355249-29-4
26 suppliers
$65.00/100mg