Sodium Hydroxide → 3-Fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}aniline

HRID 2192174Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:22]C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][O:20][CH3:21])[C:10]=12.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][O:20][CH3:21])[C:10]=12)[NH2:22]

Participants

Conditions

Temperature: 90 °C

Procedure

63 mg (0.18 mmol) of N-(3-fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}phenyl)acetamide are dissolved in 5 ml of ethanol. 2 ml of 20% strength aqueous sodium hydroxide solution are added, and the mixture is stirred at 90° C. overnight. The reaction mixture is then partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The aqueous solution is extracted with ethyl acetate and the combined organic phases are washed with 1N aqueous sodium hydroxide solution. The organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure. The product is reacted further without purification.

Workup

customThe reaction mixture is then partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
extractionThe aqueous solution is extracted with ethyl acetate
washthe combined organic phases are washed with 1N aqueous sodium hydroxide solution
dry with materialThe organic phases are dried over magnesium sulfate
customthe solvent is removed under reduced pressure
customThe product is reacted further without purification

Sources & evidence

ORD record: ord-50bf8ad04cd8421a9686db483d298bdc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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