Potassium Carbonate → N-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)pivalamide

HRID 1157786Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH:23]=[N:22][C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:20]1.CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[CH3:12][O:11][C:5]1[CH:4]=[N:3][C:2]([N:19]2[CH:23]=[N:22][C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:27])[CH3:29])=[N:20]2)=[C:7]2[NH:8][CH:9]=[CH:10][C:6]=12

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine (250 mg, 1.101 mmol), potassium carbonate (457 mg, 3.30 mmol), copper(I) iodide (105 mg, 0.551 mmol), N-(1H-1,2,4-triazol-3-yl)pivalamide and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (78 mg, 0.551 mmol) in 1,4-dioxane (2 mL) were heated up at 110° C. for 13 h. The reaction mixture was filtered through a silica gel pad and concentrated under reduced pressure. The resulting crude was purified by prep HPLC to give N-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)pivalamide (90 mg, 26%) as pale yellow oil. LCMS: m/e 315.05 (M+H)+, ret time 1.55 min (method 8).

Workup

filtrationThe reaction mixture was filtered through a silica gel pad
concentrationconcentrated under reduced pressure
customThe resulting crude was purified by prep HPLC

Sources & evidence

ORD record: ord-80c371fb3593471aadecb0494cfb88c7
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807676B2

Reaction notes

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