Sodium Hydroxide → 3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline

HRID 2192162Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:29]C(=O)C)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH:16]=[C:17]([CH3:18])[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]([CH3:18])[C:10]=12)[NH2:29]

Participants

Conditions

Temperature: 90 °C

Procedure

267 mg (0.59 mmol) of N-[3-fluoro-4-({3-methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]-pyridin-4-yl}oxy)phenyl]acetamide are dissolved in 10 ml of ethanol. 5 ml of 20% strength aqueous sodium hydroxide solution are added, and the reaction mixture is heated at 90° C. overnight. Most of the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate and shaken with sodium carbonate solution. The organic phase is washed with sodium chloride solution and dried over magnesium sulfate, and the solvent is removed under reduced pressure.

Workup

customMost of the solvent is removed under reduced pressure
washThe organic phase is washed with sodium chloride solution
dry with materialdried over magnesium sulfate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-b5c02ffbf2064786b65f31b1032437f1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

Loading…