1H-Pyrrolo[2,3-b]pyridine, 5-methoxy-1-(phenylsulfonyl)- synthesis
- Product Name:1H-Pyrrolo[2,3-b]pyridine, 5-methoxy-1-(phenylsulfonyl)-
- CAS Number:397842-89-6
- Molecular formula:C14H12N2O3S
- Molecular Weight:288.32
1310-73-2
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![5-METHOXY-1H-PYRROLO[2,3-B]PYRIDINE](/CAS/GIF/183208-36-8.gif)
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1939-99-7
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Yield:397842-89-6 94%
Reaction Conditions:
with N-benzyl-N,N,N-triethylammonium chloride in dichloromethane;
Steps:
R.1 2-methyl-1H-pyrrolo[2,3-b]pyridin-5-ol
Reference Example 1 2-methyl-1H-pyrrolo[2,3-b]pyridin-5-ol To a solution of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (920 mg, 6.2 mmol) (Heterocycles 50, (2) 1065-1080, 1999) in methylene chloride (20 ml) was added benzyltriethylammonium chloride (37 mg, 0.16 mmol) followed by sodium hydroxide powder (771 mg, 19.2 mmol). The mixture was cooled to 0° C. and benzylsulfonyl chloride (991 μl, 7.77 mmol) was added dropwise. The mixture was stirred at 0° C. for 15 minutes followed by 2 hours at ambient temperature. The mixture was filtered over diatomaceous earth and the filtrate was evaporated under vacuum. The residue was purified by column chromatography eluding with ethyl acetate/petroleum ether (20/80 followed by 30/70). The fractions containing the expected product were combined and evaporated to give 5-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.69 g; 94%) 1H NMR Spectrum: (DMSO d6) 3.86 (s, 3H); 6.78 (d, 1H); 7.6-7.7 (m, 3H); 7.72 (dd, 1H); 7.88 (d, 1H); 8.02-8.12 (m, 3H) MS: 289.47 [M+H]+
References:
US2003/199491,2003,A1
98-09-9
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271-63-6
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183208-35-7
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![1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-](/CAS/GIF/754214-54-5.gif)
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