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

HRID 2192166Notes

Reaction equation

[CH:1]1([C:4]2[C:12]3[C:7](=[N:8][CH:9]=[CH:10][C:11]=3[O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][C:15]=3[F:24])[N:6](S(C3C=CC(C)=CC=3)(=O)=O)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[C:12]3[C:7](=[N:8][CH:9]=[CH:10][C:11]=3[O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=3[F:24])[NH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

192 mg (0.40 mmol) of N-[4-({3-cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)-3-fluorophenyl]acetamide are dissolved in 7 ml of ethanol. 3.5 ml of 20% strength aqueous sodium hydroxide solution are added, and the reaction mixture is stirred at 90° C. overnight. The reaction mixture is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. The crude product is reacted without further purification.

Workup

customThe reaction mixture is partitioned between ethyl acetate and water
extractionThe aqueous phase is extracted with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
customthe solvent is removed under reduced pressure
customThe crude product is reacted without further purification

Sources & evidence

ORD record: ord-15ae91894c1b40aba01487763f9b237f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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