4-Toluenesulfonyl chloride → N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

HRID 2192158Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[NH:4][CH:3]=1.C([Li])CCC.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

3.23 g (8.87 mmol) of N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}acetamide are dissolved in 500 ml of THF and cooled to −78° C. 3.90 ml (9.76 mmol) of a 2.5M n-butyllithium solution are added, and the mixture is stirred for 15 min. 1.86 g (9.76 mmol) of p-toluenesulfonyl chloride are then added dropwise as a solution in 20 ml of THF. The reaction solution is allowed to warm to RT and stirred for one hour. Sodium bicarbonate solution is then added, and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure.

Workup

temperatureto warm to RT
stirringstirred for one hour
extractionthe mixture is extracted three times with ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-ac1b308175fd4fd09c730cf0f091a29f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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