Sodium Methoxide → N-(3-Fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}phenyl)acetamide

HRID 2192173Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][C:21]=3[O:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][C:25]=3[F:34])[N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH:15]=2)(=O)=O)=CC=1.[CH3:45][O-].[Na+]>CO>[F:34][C:25]1[CH:26]=[C:27]([NH:30][C:31](=[O:33])[CH3:32])[CH:28]=[CH:29][C:24]=1[O:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]2[NH:16][CH:15]=[C:14]([CH2:13][CH2:12][O:11][CH3:45])[C:22]=12

Participants

Conditions

Temperature: 45 °C

Procedure

150 mg (0.24 mmol) of 2-{4-[4-(acetylamino)-2-fluorophenoxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl 4-methylbenzenesulfonate are dissolved in 6 ml of methanol. 0.17 ml (0.94 mmol) of a 5.4M sodium methoxide solution is added, and the mixture is stirred at 45° C. overnight. The reaction solution is partitioned between 1N aqueous sodium hydroxide solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried over magnesium sulfate. The solvent is removed under reduced pressure. The product obtained is reacted without further purification.

Workup

customThe reaction solution is partitioned between 1N aqueous sodium hydroxide solution and ethyl acetate
extractionThe aqueous phase is extracted with ethyl acetate
dry with materialthe combined organic phases are dried over magnesium sulfate
customThe solvent is removed under reduced pressure
customThe product obtained
customis reacted without further purification

Sources & evidence

ORD record: ord-8b35c6b5cb2b413c87433e8adb313d2c
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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