Chlorosuccinimide → N-{4-[(3-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 2192163Notes

Reaction equation

HRID 2192163 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]([F:32])([F:31])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[NH:27][CH:28]=[CH:29][C:22]=23)=[C:16]([F:30])[CH:15]=1)=[O:12].C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:29]1[C:22]2[C:23](=[N:24][CH:25]=[CH:26][C:21]=2[O:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:10]([F:31])([F:9])[F:32])=[CH:15][C:16]=2[F:30])[NH:27][CH:28]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 597409942,2,2-trifluoro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]acetamide

Product 1

HCID 59741002N-{4-[(3-Chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

233 mg (1.75 mmol) of N-chlorosuccinimide are added to a solution of 540 mg (1.59 mmol) of 2,2,2-trifluoro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]acetamide in anhydrous tetrahydrofuran (20 ml). The solution is stirred overnight. 20 ml of a saturated sodium bicarbonate solution are added, and the mixture is extracted with ethyl acetate (two times 20 ml). The combined organic phases are washed with a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. This gives a solid which is not purified any further.

Workup

  1. extractionthe mixture is extracted with ethyl acetate (two times 20 ml)
  2. washThe combined organic phases are washed with a saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives a solid which
  6. customis not purified any further

Sources & evidence

ORD record
ord-e0126ef5faa7409eb5e9ac3520ab71bb
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

Loading…