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

HRID 2205866Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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)

Sources & evidence

ORD record: ord-ba29c29b62234ba08b2c667cebdb8020
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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