Water → HCID 59490907, compound

HRID 1952226Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[NH:15][C:8]2=[CH:9][N:10]=[C:11]([O:13][CH3:14])[CH:12]=[C:7]2[C:6]=1I)=[O:4].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.[C:26](=O)([O-])[O-:27].[K+].[K+].O>COCCOC.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:15][C:8]2=[CH:9][N:10]=[C:11]([O:13][CH3:14])[CH:12]=[C:7]2[C:6]=1[C:19]1[C:18]([O:27][CH3:26])=[N:17][CH:22]=[CH:21][CH:20]=1)=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

3-Iodo-5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C3 (0.3 g, 0.9 mmol) was diluted with 1,2-dimethoxyethane (5 mL) and to the resulting solution was added PdClz2 (dppf)2 (0.074 g, 10 mol %). The reaction was heated to 90° C. and allowed to stir at this temperature for 30 minutes. Pyridyl boronic acid (0.415 g, 2.7 mmol), potassium carbonate (0.621 g, 5 mmol), and water (0.3 mL) were then added to the reaction mixture in three portions over 5 minutes. The resulting reaction allowed to stir at 90° C. for an additional minutes, then the reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through a celite plug. The filtrate was concentrated in vacuo and the resulting residue was purified using flash chromatography to provide 5-methoxy-3-(2-methoxy-pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C4 (0.075 g, 27% yield). MS: 314.2 (M+H)+.

Workup

customThe resulting reaction
stirringto stir at 90° C. for an additional minutes
temperaturethe reaction mixture was cooled to room temperature
filtrationfiltered through a celite plug
concentrationThe filtrate was concentrated in vacuo
customthe resulting residue was purified

Sources & evidence

ORD record: ord-55c1f33dbb934f8ab858ce539b4dbbf0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404845B2

Reaction notes

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