Sodium Carbonate → N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide

HRID 68617

Reaction equation

HRID 68617 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][N:14]([CH3:25])[S:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2Br)=[CH:5][CH:4]=1.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][N:14]([CH3:25])[S:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:32]([F:43])([F:42])[F:31])[CH:38]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 66869194N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide

Product 1

HCID 66868532N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of bromide 34 (1.0 g, 2.02 mmol, 1 eq) and 3-(trifluoromethyl)phenyl boronic acid (575 mg, 3.03 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) in dimethoxyethane (70 mL), was added sodium carbonate solution (9 mL of a 2 M solution) and tetrakis-triphenylphosphine palladium (233 mg, 0.1 eq). The mixture was stirred at 90° C. for 16 h, cooled to room temperature, and concentrated in vacuo. The resultant residue was partitioned between EtOAc and saturated sodium bicarbonate solution, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography (0-40% EtOAc/hexane) to give 790 mg (72%) of N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide (35). 1HNMR (CD3OD, 400 MHz): δ 7.84 (m, 3H), 7.65 (d, 1H), 7.44-7.54 (m, 3H), 7.18-7.30 (m, 5H), 7.04 (d, 1H), 6.85 (d, 2H), 5.02 (s, 2H), 4.14 (s, 2H), 3.80 (s, 3H), 2.63 (s, 3H). MS (ESI): MH+=560.1. HPLC (Method B) tR=4.57 min.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was partitioned between EtOAc and saturated sodium bicarbonate solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (0-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-6e89b36e6e7e4c7abb77e0bd3136f910
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Linked notes

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