Water → HCID 67484356, compound

HRID 2103647Notes

Reaction equation

HRID 2103647 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:18]1([CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH2:26][OH:27])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.O>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:18]1(/[CH:24]=[C:25](\[C:2]2[CH:7]=[N:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=2)/[CH2:26][OH:27])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 134334245-Bromo-2-methanesulfonylpyridineHCID 670845993-Cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67484356HCID 67484356, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Add 5-bromo-2-methanesulfonyl-pyridine (0.47 g, 2.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (163 mg, 0.2 mmol), and Na2CO3 (2.5 mL, 2.0 M, 5.0 mmol) to a solution of 3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (0.53 g, 2.2 mmol) in DMF (10 mL). Stir at 80° C. for 18 h, monitor completion of the reaction by LCMS. Treat the reaction mixture with water and extract 3 times with MTBE. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 0.72 g crude product. Purification by silica gel chromatography, eluting with gradient from 10:0 to 8:2 dichloromethane:MTBE affords 350 mg (E)-3-cyclohexyl-2-(6-methanesulfonyl-pyridin-3-yl)-prop-2-en-1-ol. MS (m/e): 296 (M+H).

Workup

  1. customcompletion of the reaction by LCMS
  2. extractionextract 3 times with MTBE
  3. customDry organic layers over sodium sulfate and remove solvents under vacuum
  4. customto obtain 0.72 g crude product
  5. customPurification by silica gel chromatography
  6. washeluting with gradient from 10:0 to 8:2 dichloromethane

Sources & evidence

ORD record
ord-7955e4bffd9f4a9ca44f89b82a1bb47f
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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