ChemicalBook CAS DataBase List 5-bromothieno[2,3-b]pyridine

5-bromothieno[2,3-b]pyridine synthesis

4synthesis methods

Product Name:5-bromothieno[2,3-b]pyridine
CAS Number:21344-24-1
Molecular formula:C7H4BrNS
Molecular Weight:214.08

21344-28-5

21344-24-1

General procedure for the synthesis of 5-bromothieno[2,3-b]pyridine from 5-aminothieno[2,3-b]pyridine: In Example 16E, 5-aminothieno[2,3-b]pyridine (1.35 g, 9.0 mmol) was reacted with isoamyl nitrite (Aldrich, 2.10 g, 18.0 mmol) and copper(II) bromide ( Aldrich, 4.03 g, 18.0 mmol) in acetonitrile (20 mL) at room temperature overnight. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution (20 mL) and subsequently extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with brine (2 x 30 mL) and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, v/v 80/20, Rf = 0.80) to afford 5-bromothieno[2,3-b]pyridine (1.03 g, 53.0% yield). The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.61 (d, J=2.03 Hz, 1H), 8.21 (d, J=2.37 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H), 7.22 (d, J=6.10 Hz, 1H). Mass spectra (DCI/NH3) showed m/z 214 (M+1)+ and 216 (M+1)+.

21344-28-5
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21344-24-1
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Yield: 53%

Reaction Conditions:

with copper(ll) bromide;isopentyl nitrite in acetonitrile at 20;

Steps:

16.E 5-Bromothieno[2,3-b]pyridine
Example 16E 5-Bromothieno[2,3-b]pyridine The product of Example 16D (1.35 g. 9.0 mmol) was treated with iso-amylnitrite (Aldrich. 2.10 g. 18.0 mmol) and CuBr₂ (Aldrich, 4.03 g. 18.0 mmol) in MeCN (20 mL) at ambient temperature overnight. The reaction mixture was quenched with saturated NH₄Cl (20 mL) and then extracted with EtOAc (3*50 mL). The combined extracts were washed with brine (2*30 mL) and concentrated. The residue was purified with chromatography (SiO₂, EtOAc/hexane, v. 80/20. R^f=0.80) to give the title compound (1.03 g, yield, 53.0%). ¹H NMR (300 MHz, CDCl₃) 8 ppm 7.22 (d, J=6.10 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H). 8.21 (d, J=2.37 Hz, 1H), 8.61 (d, J=2.0(3 Hz, 1H):MS (DCI/NH₃) m/z 214 (M+1)⁺, 216 (M+1)⁺.

References:

Abbott Laboratories US2008/153860, 2008, A1 Location in patent:Page/Page column 25

5-broMothieno[2,3-b]pyridine-2-carboxylic acid

1242336-81-7
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21344-24-1
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References

56267-50-6 Synthesis

56267-50-6
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2065-75-0 Synthesis

2065-75-0
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21344-24-1
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$60.00/1g

References

21344-35-4
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21344-24-1
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References