Potassium Hydroxide → 4-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol

HRID 222573Notes

Reaction equation

HRID 222573 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-:18].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C(OCC)C>[CH3:17][S:14]([N:11]1[CH2:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:18])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 58111158HCID 58111158, compound

Product 1

HCID 579301164-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenolYield 85%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-bromo-phenyl)-1-methanesulfonyl-1,2,3,6-tetrahydro-pyridine (23.50 g, 74.32 mmol), potassium hydroxide (14.72 g, 222.95 mmol), 2-di-tert-butylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (2.52 g, 5.95 mmol) and tris(dibenzylideneacetone)dipalladium (0) (1.36 g, 1.49 mmol) is purged with nitrogen, and then deoxygenated 1,4-dioxane (150 mL) and deoxygenated water (150 mL) are added. The mixture is stirred at 100° C. for 1 h. The mixture is cooled to 23° C. and 1 M aq hydrochloric acid is added until pH 2-3. The aqueous layer is extracted with ethyl acetate. The organic layers are combined, dried over anhydrous sodium sulfate, filtered, and the solvent is removed to obtain a red solid. Diethyl ether is added and the solid is filtered to obtain 16 g of the title compound as an off-white solid. MS (m/z) 254 (M+1).

Workup

  1. customis purged with nitrogen
  2. customdeoxygenated 1,4-dioxane (150 mL) and deoxygenated water (150 mL)
  3. additionare added
  4. temperatureThe mixture is cooled to 23° C.
  5. addition1 M aq hydrochloric acid is added until pH 2-3
  6. extractionThe aqueous layer is extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed
  10. customto obtain a red solid
  11. filtrationthe solid is filtered

Sources & evidence

ORD record
ord-54fb6e78c2da4bf6ab8d671a417a7d04
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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