Potassium Carbonate → tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate

HRID 68594Notes

Reaction equation

HRID 68594 reaction equation
Br[C:2]1[CH:16]=[C:15]([CH2:17][N:18]([CH3:30])[S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=2)(=[O:21])=[O:20])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[F:31][C:32]1[CH:33]=[C:34]([C:2]2[CH:16]=[C:15]([CH2:17][N:18]([CH3:30])[S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=3)(=[O:21])=[O:20])[CH:14]=[CH:13][C:3]=2[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2763243(3-Fluoro-5-methoxyphenyl)boronic acidHCID 67527857tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate

Product 1

HCID 67528984tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetateYield 45.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butyl 2-(2-bromo-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxy)acetate (10) (140 g, 0.27 mol, 1 eq), 3-fluoro-5-methoxyphenylboronic acid (45.7 g, 0.27 mol, 1 eq, Combi-Blocks Inc., San Diego, Calif., USA) and potassium carbonate (111 g, 0.81 mol, 3 eq) in dioxane/water (3:1, 800 mL) was added tetrakis(triphenylphoshine)palladium (3.08 g, 2.7 mmol, 0.01 eq). The mixture was heated at 60° C. for 3 h under N2. Solvent was evaporated, and the solid was dissolved in DCM and filtered. The DCM was evaporated and the crude product was recrystallized from ethanol to yield tert-butyl 2-(3-fluoro-5-methoxyphenyl)-4-((3-chloro-4-fluoro-N-methylphenylsulfonamido)methyl)phenoxyacetate (11) (70 g, 41%).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe solid was dissolved in DCM
  3. filtrationfiltered
  4. customThe DCM was evaporated
  5. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-b06351137ece4834829ce0e6c47656fa
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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