3-Bromo-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester synthesis
- Product Name:3-Bromo-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester
- CAS Number:1104630-92-3
- Molecular formula:C9H6BrNO2S
- Molecular Weight:272.12
![METHYL 3-AMINOTHIENO[3,2-B]PYRIDINE-2-CARBOXYLATE](/CAS/GIF/111042-90-1.gif)
111042-90-1
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Yield:1104630-92-3 92.2%
Reaction Conditions:
with hydrogen bromide;copper(I) bromide;sodium nitrite in water at 0 - 5; for 1.5 h;
Steps:
1.A Step A.
Methyl 3-bromothieno[3,2-b]pyridine-2-carboxylate
Step A.
Methyl 3-bromothieno[3,2-b]pyridine-2-carboxylate
To a solution of copper (I) bromide (1.450 g, 10.10 mmol) in HBr (24 mL, 210 mmol) at 0-5° C., methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate (2.00 g, 9.60 mmol) was added.
To the mixture at this temperature a solution of sodium nitrite (0.796 g, 11.5 mmol) in water (12 mL) was added dropwise over 30 min.
The reaction was continued at 0-5° C. for 1 h.
The reaction mixture was slowly poured into iced water containing 20 g of NaHCO3 and extracted with DCM (2 times).
The combined organic phases were washed with water and brine, dried over Na2SO4, concentrated under reduced pressure to give 2.41 g (92.2% yield) of the sub-title compound as a yellow solid. LCMS calc. for C9H7BrNO2S (M+H)+: m/z=271.9. found: 272.0.
References:
US2015/57265,2015,A1 Location in patent:Paragraph 0808; 0809
1851-22-5
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38180-46-0
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