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

HRID 1452543
ノート
印刷プレビュー

反応式

HRID 1452543 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

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, 3:1)

出典と根拠

ORDレコード
ord-bec3d449dbd64d999619eff62721c879
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07473703B2

反応ノート

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