Boron trifluoride etherate → N-(4-{1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

HRID 1452543Notes

Reaction equation

HRID 1452543 reaction equation
O[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:28])[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:14][CH:13]=1)[C:3]1[N:4]([CH2:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:11][O:10][CH2:9][CH2:8][N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH2:2][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:28])[S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 10237663N-(4-{1-Hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

Product 1

HCID 10215928N-(4-{1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 16 mg (0.04 mmol) of N-(4-{1-hydroxy-1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-methyl}-phenyl)-N-methyl-benzenesulfonamide (Example 7) in 1.5 mL CH2Cl2 at 0° C. were added 620 μL (3.88 mmol) of triethylsilane followed by 100 μL (0.79 mmol) of boron trifluoride diethyl etherate dropwise. The mixture was warmed to room temperature and stirred for 2.5 h. After this time, the reaction mixture was cooled to 0° C., quenched by the addition of a saturated aqueous solution of sodium bicarbonate, allowed to warm to room temperature, 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, 3:1) to give the title compound.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  2. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate
  3. temperatureto warm to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 3:1)

Sources & evidence

ORD record
ord-bec3d449dbd64d999619eff62721c879
Source dataset
uspto-grants-2009_01
Patent number
US07473703B2

Reaction notes

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