tert-Butanol → tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

HRID 2205866Notizen

Reaktionsgleichung

C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[N:21](S(C)(=O)=O)[C:15]=2[CH:14]=1.C(O)(C)(C)C>C1COCC1.O>[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[NH:21][C:15]=2[CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

DBU (0.193 mL, 1.289 mmol) was added to a solution of tert-butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (9) (0.517 g, 1.172 mmol) and tert-butanol (0.224 mL, 2.343 mmol) in THF (11.7 mL). The reaction mixture was stirred at 40° C. for 1 hr. It was then diluted with water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was adsorbed on silica and purified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column) to afford the title compound as a white solid (271 mg, 58%). 1H NMR (500 MHz, CDCl3) 1.71 (s, 9H), 6.75 (s, 1H), 7.50 (s, 1H), 8.02 (s, 1H), 8.38 (s, 1H), 8.50 (s, 1H), 8.66 (s, 1H).

Aufarbeitung

extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column)

Quellen und Nachweise

ORD-Eintrag: ord-ba29c29b62234ba08b2c667cebdb8020
Quelldatensatz: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09371319B2

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