SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2009, Pages 456-460

Facile synthesis of fluorinated pyrrolo[2,3-b]pyridines

(4) Groth, Ulrich a Iaroshenko, Viktor O a Wang, Yan a Wesch, Thomas a

a UNIVERSITY OF KONSTANZ (Germany)

Author keywords

Amine; Annulation; Electrophilic aromatic substitution; Fluorine; Pyridine; Pyrrol

Indexed keywords

EID: 62249206611 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087530 Document Type: Article

Times cited : (2)

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43
- 62249191038
- 1-tert-Butyl-4-[chloro(difluoro)methyl, 6-phenyl-1Hpyrrolo[ 2,3-b]pyridine-3- carbonitrile (11e) Colorless solid (0.65g, 90, mp 234°C (from EtOH, 1H NMR (400 MHz, DMSO-d6, δ, 1.87 (9 H, s, CH3, 7.53 (3 H, br m, 8.07 (1 H, s, 8.18 (2 H, d, 3JCH, 7.8 Hz, 8.70 (1 H, s, 13C NMR (100.5 MHz, DMSO-d6, δ, 28.9, 59.5, 81.9, 109.4 (t, 3JCF, 6.4 Hz, 112.8 (t, 3J CF, 2.4 Hz, 114.9, 124.6, t, 1JCF, 290 Hz, 126.9, 129.0, 129.6, 135.2 (t, 2JCF, 30 Hz, 137.8, 139.7, 148.0, 151.3. MS: m/z, 361(13, M, 2, 359(36, M, 304(23, 303(100, 269(16, 268(75, 5713, Anal. Calcd for C19H16ClF2N3: C, 63.42; H, 4.48; Cl, 9.85;
- 3: C, 63.42; H, 4.48; Cl, 9.85; F, 10.56; N, 11.68. Found: C, 63.50; H, 4.53; N, 11.75.

44
- 62249123658
- 2.
- 2.

45
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46
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48
- 62249086784
- The Procedure for the Synthesis of (E)-1-tert- Butyl-5-(4,4,4-trifluoro-3-oxobut-1-enylamino)-1H-pyrrole-3-carbonitrile (15) 5-Amino-1-tert-butyl-1H-pyrrole-3-carbonitrile (0.66 g, 4 mmol) and 14 (0.68 g, 4.4 mmol) were dissolved in abs. DMF (10 mL) and heated under inert atmosphere at 85°C for 12 h. The solution was evaporated under reduced pressure, treated with H 2O, and dried under reduced pressure. Afterwards, the residue was subjected to column chromatography over SiO2. Colorless solid (0.78 g, 68, mp 116-118 ° C; Rf, 0.75 (hexane-EtOAc, 5:1, 1H NMR (400 MHz, CDCl3, d, 1.59 (9 H, s, CH 3, 5.68 (1 H, d, 3JHH, 8 Hz, 6.20 (1 H, s, 7.13 (1 H, s, 7.29 (1 H, dd, 3JHH, 8 Hz, 3JHH, 4 Hz, 11.80 1 H, d, 3JHH
- 3O: C, 54.73; H, 4.95; F, 19.98; N, 14.73; O, 5.61. Found: C, 54.80; H, 4.98; N, 14.78.

49
- 62249111782
- Procedure for the Synthesis of 1-tert-Butyl-4, trifluoromethyl)-1H-pyrrolo[2,3-b] pyridine-3-carbonitrile (16) 1-tert-Butyl-5-(4,4,4-trifluoro-3- oxobut-1-enylamino)-1Hpyrrole-3-carbonitrile (15, 0.57 g, 2 mmol) in a 10 mL flask was melted for 5 h under inert atmosphere at 180°C (temperature of the oil bath, then the dark-green residue formed was subjected to column chromatography over SiO2. Colorless solid (0.38 g, 71, mp 161-163°C. Rf, 0.75 (hexane-EtOAc, 5:1, 1H NMR (400 MHz, CDCl3, δ, 1.78 (9 H, s, CH3, 7.41 (1 H, d, 3JHH, 4.7 Hz, H, 7.99 (1 H, s, 8.49 (1 H, d, 3JHH, 4.7 Hz, 13C NMR (100.5 MHz, CDCl3, δ, 29.0, 59.3, 82.8, 113.8 (q, 3JCF, 4.7 Hz, 114.5, 115.7, 122.8 q, 2JCF
- 3: C, 58.42; H, 4.53; F, 21.33; N, 15.72. Found: C, 58.50; H, 4.59; N, 15.71.

50
- 62249136032
- Crystallographic data (excluding structure factors) for the structure11c reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 683574 and can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk, or via
- Crystallographic data (excluding structure factors) for the structure11c reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 683574 and can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk, or via www.ccdc.cam.ac.uk/data-request/cif.

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