Sodium Hydroxide → 4-[(3-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluoroaniline

HRID 2192177Notes

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[C:19]([F:20])=[CH:18][C:17]([NH:21]C(=O)C)=[CH:16][C:15]=3[F:25])[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[C:15]([F:25])=[CH:16][C:17]([NH2:21])=[CH:18][C:19]=3[F:20])[NH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

624 mg (1.25 mmol) of N-[4-({3-cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide are dissolved in 17 ml of ethanol. 10 ml of semiconcentrated aqueous sodium hydroxide solution are added, and the reaction mixture is stirred at 90° C. for 15 h. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is washed twice with water, dried over sodium sulfate and concentrated under reduced pressure. This gives a crystalline residue.

Workup

customThe reaction mixture is partitioned between ethyl acetate and water
washThe organic phase is washed twice with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThis gives a crystalline residue

Sources & evidence

ORD record: ord-e1868c3891304200889780930c3dc0bd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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