Triethylamine → 3-[2-(4'-Ethoxybiphenyl-4-yl)ethynyl]quinuclidin-3-ol

HRID 964597Notes

Reaction equation

HRID 964597 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17]([C:19]1([OH:27])[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1)#[CH:18].C(N(CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:18]#[C:17][C:19]3([OH:27])[CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:16]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 158408841-(4-Bromophenyl)-4-ethoxybenzene

Product 1

HCID 190775473-[2-(4'-Ethoxybiphenyl-4-yl)ethynyl]quinuclidin-3-olYield 21.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 4-bromo-4'-ethoxybiphenyl (1.1 g), 3-ethynyl-3-hydroxyquinuclidine (600 mg), bis(triphenylphosphine)-palladium (II) chloride (140 mg), copper (I) iodide (70 mg) and dry triethylamine (5.0 ml) in dry dimethylformamide (20 ml) was stirred at 90° C. under an atmosphere of argon for 4 hours. The dimethylformamide and triethylamine were removed by evaporation and the residue was treated with saturated sodium carbomate solution (20 ml). The solid obtained was collected by filtration and crystallised from dimethylformamide to give 3-[2-(4'-ethoxybiphenyl-4-yl)ethynyl]quinuclidin-3-ol (300 mg) as a soild, m.p. 255-256° C.; microanalysis, found C, 79.1; H, 7.3; N, 3.9%; C23H25NO2 requires C, 79.5; H, 7.3; N, 4.03%; NMR (DMSO-d6): 1.2-.1.4(3H, t), 1.52-1.71(1H, m), 1.8-2.0(3H, m), 2.6-2.98(5H, m), 3.05-3.2(1H, m), 4.0-4.16(2H, q), 5.51-5.62(1H, br), 6.95-7.05(2H, d), 7.4-7.5(2H, d) an 7.57-7.68(4H, m); m/z 348 (M+H).

Workup

  1. customThe dimethylformamide and triethylamine were removed by evaporation
  2. additionthe residue was treated with saturated sodium carbomate solution (20 ml)
  3. customThe solid obtained
  4. filtrationwas collected by filtration
  5. customcrystallised from dimethylformamide

Sources & evidence

ORD record
ord-ba23980c790149fcac9c42f5040a644a
Source dataset
uspto-grants-1998_06
Patent number
US05770608

Reaction notes

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