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 2053680ノート

反応式

HRID 2053680 の反応式
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]

参加物

7

反応物 3

HCID 5171346N-(4-bromophenyl)-N-methylbenzenesulfonamideHCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrroleHCID 178418306HCID 178418306、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-179d44d4c97840c6b58dfc33a4e132ae
出典データセット
uspto-grants-2008_02
特許番号
US07326812B2

反応ノート

読み込み中…