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

HRID 2103624
Notes
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Reaction equation

HRID 2103624 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-32af3048a75348b8b7231f209bbace06
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576108B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes