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Volumn , Issue 2, 2008, Pages 185-188

Synthesis of tetrasubstituted 2-aryl-3-arylsulfonyl pyrroles: Unexpected regioselectivity in directed ortho-metallation reactions

(4) Bailey, Nick a Demont, Emmanuel a Garton, Neil a Seow, Hui Xian a

a GLAXOSMITHKLINE (United Kingdom)

Author keywords

3 sulfonyl pyrrole; Directed ortho metallation; Palladium; Phenylsulfonyl fluoride; Suzuki coupling

Indexed keywords

2 PHENYL 3 PHENYLSULFONYL PYRROLE; DEUTERIUM; HALOGEN; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; METALLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 38849118352 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000880 Document Type: Article

Times cited : (6)

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29
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30
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31
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- 1H NMR of the crude reaction. This ratio was at least 95:5 at 50°C. Lower temperatures were not considered.

32
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33
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- See also ref. 14d
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34
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- +.
- +.

35
- 38849198121
- Typical Procedures: Compound 5b: To a solution of 3-bromo-1-[tris(1-methyl-ethyl)silyl]-1H-pyrrole (12.8 g, 42.4 mmol, 1 equiv) in THF (200 mL) at -78°C under nitrogen was slowly added n-BuLi (2.5 M in hexanes, 17.8 mL, 44.5 mmol, 1.05 equiv) over 3 min and the resulting mixture was stirred for 15 min at this temperature. Phenylsulfonyl fluoride (7.5 g, 46.6 mmol, 1.1 equiv) in THF (20 mL) was added via syringe over 5 min and the resulting mixture was stirred for 45 min at this temperature, then partitioned between EtOAc (200 mL) and brine (100 mL, The two layers were separated and the aqueous phase was extracted with EtOAc (20 mL, The combined organic phases were washed with brine (2 x 50 mL, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in THF (200 mL) and TBAF (1 M in THF, 42 mL, 1 equiv) was added and the resulting mixture was stirred for 30 min and then dissolved with EtOAc 200 mL, The organic phase was washed
- +.

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