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Tetrahydrofuran → (E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide

HRID 2103624
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HRID 2103624 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:20]1(/[CH:25]=[C:26](\B2OC(C)(C)C(C)(C)O2)/[CH2:27][OH:28])[CH2:24][CH2:23][CH2:22][CH2:21]1.[F-].[Cs+].C1COCC1>O1CCOCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:20]1(/[CH:25]=[C:26](\[C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:27][OH:28])[CH2:24][CH2:23][CH2:22][CH2:21]1
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참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 35270444-bromo-N-(2-pyridin-2-ylethyl)benzenesulfonamideHCID 67084716(E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

생성물 1

HCID 67084671(E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide수율 49.2%

시약·촉매·용매

2
HCID 178420553HCID 178420553, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

Heat a suspension of 4-bromo-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide (1.67 g, 4.89 mmol), (E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.60 g, 6.36 mmol), caesium fluoride (2.23 g, 14.7 mmol) and tetrakis(triphenylphosphino)palladium(0) (565 mg, 489 μmol) in 50 mL dioxane to reflux for 2 d and cool to r.t. thereafter. After addition of 50 mL THF filtrate the resulting suspension, wash with dichloromethane and concentrate under reduced pressure. Further purify the resulting brown oil by column chromatography, eluting with a gradient from 100:0 to 0:100 hexanes:ethyl acetate to afford (E)-4-(2-cyclopentyl-1-hydroxymethyl-vinyl)-N-(2-pyridin-2-yl-ethyl)-benzenesulfonamide (929 mg) as a pale yellow oil. MS (m/e): 387 (M+H).

후처리

  1. temperatureHeat
  2. temperatureto reflux for 2 d
  3. washwash with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customFurther purify the resulting brown oil by column chromatography
  6. washeluting with a gradient from 100:0 to 0:100 hexanes

출처 및 근거

ORD 기록
ord-32af3048a75348b8b7231f209bbace06
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576108B2

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