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

HRID 2216544
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HRID 2216544 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-19d72f5df91148338daa5cbff205fd86
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112606B2

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