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

HRID 1791021ノート

反応式

HRID 1791021 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:33])[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1)(O)[C:12]([F:15])([F:14])[F:13])[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:33])[S:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:25])=[O:26])=[CH:19][CH:18]=1)[C:12]([F:13])([F:14])[F:15])[CH3:2]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 21943462N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

生成物 1

HCID 21943465N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-phenyl)-N-methyl-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 32 mg (0.07 mmol) of N-(4-{1-[1-(2-ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide (Example 78) in 2 mL of CH2Cl2 at 0° C. were added 1.05 mL (6.57 mmol) of triethylsilane followed by 167 μL (1.32 mmol) of boron trifluoride diethyl etherate dropwise. The mixture was warmed to room temperature and stirred for 1.75 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, 4:1) to give the title compound.

後処理

  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, 4:1)

出典と根拠

ORDレコード
ord-8c4550540a824d66b849dd341f27b37d
出典データセット
uspto-grants-2006_07
特許番号
US07071358B2

反応ノート

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