Sodium Hydroxide → 4-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

HRID 2192169Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][C:14]=2[F:23])[N:5](S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[F:23])[NH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

50 mg (0.11 mml) of N-[4-({3-ethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide are dissolved in 3 ml of ethanol. 1 ml of 1N aqueous sodium hydroxide solution is added, and the mixture is stirred at 90° C. overnight. The reaction solution is partitioned between ethyl acetate and saturated sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated. The crude product obtained is reacted without further purification.

Workup

customThe reaction solution is partitioned between ethyl acetate and saturated sodium bicarbonate solution
extractionThe aqueous phase is extracted with ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-bc24fcb754ea49bf943b26c4654d88e5
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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