METHYL 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBOXYLATE synthesis
- Product Name:METHYL 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBOXYLATE
- CAS Number:59812-35-0
- Molecular formula:C11H9ClO3S
- Molecular Weight:256.71
Yield:59812-35-0 50 g
Reaction Conditions:
with pyridine;thionyl chloride
Steps:
2.1 Synthesis of Compound 100 ((3-(4-(2-(Ethylamino)ethyl)phenoxy)-6-hydroxybenzo[b]thiophen-2-yl)(4-fluoro-2,6-dimethylphenyl)methanone)
In Step 1, 100 grams of Compound 32 was dissolved thionyl chloride and pyridine. Methanol was added to the solution to afford Compound 33. Compound 33 was recrystallized to obtain 50 grams of pure product. The H-NMR was clean. In Step 2, 25 grams of Compound 32 was subjected to 1.3 eq of n-butyl lithium and Compound 34. After column purification 9.8 grams of pure Compound 35 was isolated. The H-NMR was clean. In Step 3, 3.5 grams of Compound 35 was reacted with Boc-anhydride in the presence of triethylamine to afford 5 grams of Compound 37 after work-up and purification. In Step 4, 4.5 grams of Compound 37 was dissolved in DMF and then Cesium Carbonate and Compound 35 were added to afford Compound 38. Compound 38 was purified by column chromatography to afford 6.8 grams of pure compound. H-NMR was clean and HPLC purity was 96%. In Step 5, to a solution of 6.2 grams of Compound 38 in DMF was added iodoethane and sodium hydride. After work-up and column purification 4.4 grams of Compound 39 was isolated. H-NMR was clean. In Step 6, 2 grams of Compound 39 was exposed to BBr3 to afford Compound 100. H-NMR was clean. HPLC purity was 96.5%.
References:
US2018/230123,2018,A1 Location in patent:Paragraph 0619-0620
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75998-29-7
12 suppliers
$63.89/250mg
59812-35-0
8 suppliers
inquiry