4-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamide → N-(4-Benzoylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

HRID 1889673Notes

Reaction equation

HRID 1889673 reaction equation
[Cl:1][C:2]1[C:3]([OH:34])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:33]=[CH:32][C:25]([C:26](N(OC)C)=[O:27])=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:35]1([Mg]Br)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[S:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[OH:34])(=[O:11])=[O:10])=[CH:33][CH:32]=1)(=[O:27])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 585315364-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamideHCID 178418255HCID 178418255, compound

Product 1

HCID 58531392N-(4-Benzoylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamideYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamide (0.105 g, 0.20 mmol) in THF (2 mL) was added phenylmagnesium bromide (3M in ether, 0.267 mL, 0.800 mmol). The resulting mixture was stirred at rt overnight. The mixture was quenched by adding cold saturated aq. NH4Ac solution and extracted with DCM. The combined organic extracts were dried and concentrated. The residue was purified by preparative HPLC. The desired fractions were combined, concentrated and lyophilized to dryness to give the title compound (46 mg, 42%) as a tan solid. MS (ESI): 544.1 (M+H)+.

Workup

  1. customThe mixture was quenched
  2. additionby adding cold saturated aq. NH4Ac solution
  3. extractionextracted with DCM
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8669bf85891f4e3eab51f9462b7982fa
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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