N-(4-bromophenyl)-N-methylbenzenesulfonamide → N-(4-{1-Hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

HRID 1452542Notes

Reaction equation

HRID 1452542 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:18])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[CH3:24][O:25][CH2:26][CH2:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH:33]=[O:34]>C1COCC1.CCCCC>[OH:34][CH:33]([C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:18])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1)[C:29]1[N:28]([CH2:27][CH2:26][O:25][CH3:24])[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 5171346N-(4-bromophenyl)-N-methylbenzenesulfonamideHCID 176210051-(2-methoxyethyl)-1H-pyrrole-2-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 10237663N-(4-{1-Hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a solution of 1.49 g (4.59 mmol) of N-(4-bromophenyl)-N-methyl benzenesulfonamide (see Preparative Example A, Step C) in 37.5 mL THF at −78° C. was added dropwise 5.94 mL (10.10 mmol) of a 1.7 M solution of tert-BuLi in pentane and the resultant mixture was stirred at −78° C. for 15 min. To this mixture was then added a solution of 1.01 g (6.59 mmol) of N-methoxyethylpyrrole-2-carboxaldehyde in 6 mL THF and the mixture was allowed to gradually warm to −30° C. over a 4 h period. After this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 13:7) to give the title compound.

Workup

  1. customAfter this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 13:7)

Sources & evidence

ORD record
ord-fd30f9b6b0964a11877f0381617afb85
Source dataset
uspto-grants-2009_01
Patent number
US07473703B2

Reaction notes

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