4-Fluorobenzenesulfonyl chloride → N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide

HRID 68616Notes

Reaction equation

HRID 68616 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH3:17])=[CH:11][C:10]=2[Br:18])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:17])[S:28]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)(=[O:30])=[O:29])=[CH:11][C:10]=2[Br:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 63045147(4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine

Product 1

HCID 66869194N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate 33 (2.7 g, 8.0 mmol, 1 eq) in DCM (10 mL) was added 4-fluorobenzene-1-sulfonyl chloride (1.9 g, 9.6 mmol, 1.2 eq) and DIEA (2.8 mL, 16.0 mmol, 2 eq). After stirring at room temperature for 1 h, the reaction was washed with saturated NaHCO3 and brine, dried (Na2SO4), and concentrated in vacuo. The crude product was purified via silica gel chromatography (0-40% EtOAc/hexane) to give 2.48 g (63%) of N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide (34).

Workup

  1. washthe reaction was washed with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified via silica gel chromatography (0-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-b2e061bbd6374298b51da5dc80af701b
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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