4-(4-Amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamide → 4-[4-({[4-bromo-3-(pentafluoro-lambda6-sulfanyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide

HRID 1428416Notes

Reaction equation

HRID 1428416 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[S:11]([F:16])([F:15])([F:14])([F:13])[F:12].[NH2:17][C:18]1[CH:34]=[CH:33][C:21]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=2)=[CH:20][C:19]=1[F:35]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:17][C:18]2[CH:34]=[CH:33][C:21]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=3)=[CH:20][C:19]=2[F:35])=[O:10])=[CH:4][C:3]=1[S:11]([F:16])([F:12])([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 468352194-(4-Amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamideHCID 867012911-Bromo-4-isocyanato-2-(pentafluoro-lambda6-sulfanyl)benzene

Product 1

HCID 575208884-[4-({[4-bromo-3-(pentafluoro-lambda6-sulfanyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 1-bromo-4-isocyanato-2-(pentafluoro-λ6-sulfanyl)benzene was dissolved in DCM (70 mL). 4-(4-amino-3-fluorophenoxy)-N-methylpicolinamide (1.75 g, 6.71 mmol, 0.8 eq) was added at room temperature under N2. The mixture was stirred at room temperature for about 30 min, a lot of solid precipitated. DCM (30 mL) was added and made the mixture stirred at room temperature for 18 hrs. The solid was collected by filtration, washed with DCM (50 mL), and dried under high vacuum to afford 2.9 g of the title compound as a white solid.

Workup

  1. customa lot of solid precipitated
  2. additionDCM (30 mL) was added
  3. stirringstirred at room temperature for 18 hrs
  4. filtrationThe solid was collected by filtration
  5. washwashed with DCM (50 mL)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-accd4d28638e4e0fbfd07cded7444d3d
Source dataset
uspto-grants-2015_01
Patent number
US08937088B2

Reaction notes

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