Water → HCID 69059481, compound

HRID 2103614Notes

Reaction equation

HRID 2103614 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=1.[F-].[Cs+].[CH:13]1([CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1.O>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]1(/[CH:18]=[C:19](\[C:2]2[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 670847173-Cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-olHCID 674844052-Bromo-4-(methylsulfonyl)thiophene

Product 1

HCID 69059481HCID 69059481, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Add 2-bromo-4-methanesulfonyl-thiophene (241 mg, 1.0 mmol), caesium fluoride ( 304 mg, 2.0 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (58 mg, 0.05 mmol) to a solution of 3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (252 mg, 1.0 mmol) in THF. Stir at 50° C. for 24 h, monitore completion of the reaction by LCMS. Treat the reaction mixture with water and extract with ethyl acetate. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 405 mg crude product. Purify by silica gel chromatography, eluting with gradient from 9:1 to 1:1 hexane:ethyl acetate to obtain 118 mg purified product. MS (m/e): 309.0 (M+Na).

Workup

  1. custommonitore completion of the reaction by LCMS
  2. extractionextract with ethyl acetate
  3. customDry organic layers over sodium sulfate and remove solvents under vacuum
  4. customto obtain 405 mg crude product
  5. customPurify by silica gel chromatography
  6. washeluting with gradient from 9:1 to 1:1 hexane
  7. customethyl acetate to obtain 118 mg
  8. custompurified product

Sources & evidence

ORD record
ord-c51b99adf5324355a8e16c09c68d36f5
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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