ChemicalBook CAS DataBase List 5-CHLORO-1H-PYRROLO[3,2-B] PYRIDINE

5-CHLORO-1H-PYRROLO[3,2-B] PYRIDINE synthesis

8synthesis methods

Product Name:5-CHLORO-1H-PYRROLO[3,2-B] PYRIDINE
CAS Number:65156-94-7
Molecular formula:C7H5ClN2
Molecular Weight:152.58

3-Pyridinamine, 6-chloro-2-[(1E)-2-ethoxyethenyl]-

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Yield:65156-94-7 71%

Reaction Conditions:

Stage #1:6-chloro-2-[(E)-2-ethoxyvinyl]pyridin-3-amine with hydrogenchloride in methanol;water at 75; for 21 h;
Stage #2: with potassium carbonate in ethyl acetate

Steps:

19 PREPARATION 19 5-Chloro-1H-pyrrolo[3,2-b]pyridine
The title compound of Preparation 18 (1.01 g, 5.1 mmol) was dissolved in 20 ml methanol. 1 ml Concentrated hydrochloric acid was added and the mixture was stirred at 75 oC for 21 h. The mixture was evaporated under reduced pressure and the residue was partitioned between saturated potassium carbonate solution and ethyl acetate. The organic layer was dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate-hexane, 33:67) to yield 0.55 g (3.6 mmol, 71%) of the title compound as a pale yellow solid. Purity 95%. [0284] ¹H NMR (300 MHz, CHLOROFORM-d + DMSO-d6) δ ppm 9.85 (br. s, 1H), 7.67 (d, J = 8.5 Hz, 1H), 7.47 (m, 1H), 7.10 (d, J = 8.5 Hz,1H), 6.65 (m, 1H). [0285] HPLC/MS (9 min) retention time 4.27 min. [0286] LRMS: m/z 153 (M+1)

References:

Almirall, S.A.;Vidal Juan, Bernat;Alonso Diez, Juan Antonio;Buil Albero, María Antonia;Eastwood, Paul Robert;Esteve Trias, Cristina;Lozoya Toribio, María Estrella;Roberts, Richard Spurring;Vidal Gispert, Laura EP2548876, 2013, A1 Location in patent:Paragraph 0283-0286

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