Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-one

HRID 343557Notes

Reaction equation

HRID 343557 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>N1CCCCC1.[Cu]I>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:30]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 108289304-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one

Product 1

HCID 542175994-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-oneYield 80.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8082PiperidineSolvent

Procedure

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.22 g, 0.70 mmol) and 3-bromopyridine (0.70 mL, 7.0 mmol) in piperidine (2 mL) under an argon atmosphere were added tetakis(triphenylphosphine)palladium(0) (0.034 g, 4%), copper(I) iodide (0.009 g, 6%) and a small crystal of triphenylphosphine, and the mixture was heated at 80°-85° C. for 0.5 h. Ammonium chloride was added, the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 35:65 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-one as an off-white solid (0.22 g, 80%). The product was further triturated from ether-hexanes, mp 88°-89° C. Anal. (C25H27NO3.0.375 H2O) calcd: C, 75.78; H, 7.03; N, 3.53; found: C, 75.77; H, 6.89; N, 3.40.

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. dry with materialwas dried (magnesium sulfate)
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluting with 35:65 ethyl acetate

Sources & evidence

ORD record
ord-1f00afab39084d06bcdda6f346cc3a4f
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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