5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde synthesis
- Product Name:5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde
- CAS Number:881674-54-0
- Molecular formula:C10H8N2O
- Molecular Weight:172.18
881674-50-6
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881674-54-0
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Yield:881674-54-0 29%
Reaction Conditions:
with tetrapropylammonium perruthennate;4-methylmorpholine N-oxide in acetonitrile at 10 - 35; for 3 h;Molecular sieve;
Steps:
110 5-(Pyridin-2-yl)-1H-pyrrole-3-carbaldehyde
Reference Example 110
5-(Pyridin-2-yl)-1H-pyrrole-3-carbaldehyde
To a solution (50 mL) of [5-(pyridin-2-yl)-1H-pyrrol-3-yl]methanol (0.96 g) in acetonitrile were added tetra-n-propylammonium perruthenate (194 mg), N-methylmorpholine N-oxide (2.98 g) and molecular sieves 4A powder (5 g), and the mixture was stirred at room temperature for 3 hr.
The reaction mixture was diluted with ethyl acetate, filtered through celite, and the filtrate was concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1) to give the title compound as colorless crystals (yield 270 mg, 29%).
1H-NMR (CDCl3)δ: 7.14-7.18 (2H, m), 7.52 (1H, br), 7.61-7.64 (1H, m), 7.69-7.74 (1H, m), 8.49-8.51 (1H, m), 9.85 (1H, s), 10.28 (1H, br).
References:
Takeda Pharmaceutical Company Limited;Kajino, Masahiro;Hasuoka, Atsushi;Tarui, Naoki;Takagi, Terufumi EP2336107, 2015, B1 Location in patent:Paragraph 0284
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$8.00/100mg
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