N-(4-bromophenyl)-N-methylbenzenesulfonamide → N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

HRID 1452546노트

반응식

HRID 1452546 반응식
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.[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH3:25]>CCOCC.CCCCC.C1COCC1>[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([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)([OH:39])[C:35]([F:36])([F:37])[F:38])[CH3:25]

참가 물질

7

반응물 3

HCID 5171346N-(4-bromophenyl)-N-methylbenzenesulfonamideHCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrroleHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 21943462N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 75 mg (0.23 mmol) of N-(4-bromophenyl)-N-methyl-benzenesulfonamide in 4 mL of Et2O at −78° C. was added dropwise 285 μL (0.49 mmol) of a 1.7 M solution of tert-BuLi in pentane and the resultant mixture was stirred at −78° C. for 10 min. To this mixture was then added a solution of 81 mg (0.34 mmol) of N-ethoxyethyl-2-trifluoroacetylpyrrole in 3 mL THF and the mixture was allowed to gradually warm to room temperature over an 18 h period. 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, 4:1) to give the title compound.

후처리

  1. customThe 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, 4:1)

출처 및 근거

ORD 기록
ord-5d021785196443dda642d91e99f01397
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473703B2

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