3-(4-Bromophenyl)pyridine → 3-[2-(4-[3-Pyridyl]phenyl)ethenyl]-3-hydroxyquinuclidine

HRID 861407

反応式

HRID 861407 の反応式
[CH:1]([C:3]1([OH:11])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)=[CH2:2].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1>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.CN(C)C=O>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([CH:2]=[CH:1][C:3]3([OH:11])[CH:8]4[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]4)[CH2:4]3)=[CH:18][CH:17]=2)[CH:20]=1

参加物

6

反応物 2

HCID 15152413-(4-Bromophenyl)pyridineHCID 226207783-Ethenyl-3-hydroxy-1-azabicyclo[2.2.2]octane

生成物 1

HCID 540792413-[2-(4-[3-Pyridyl]phenyl)ethenyl]-3-hydroxyquinuclidine収率 29.7%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 3-ethenyl-3-hydroxyquinuclidine (673 mg), 3-(4-bromophenyl)pyridine (1.08 g), bis-(triphenylphosphine)-palladium (II) chloride (140 mg), copper (I) iodide (70 mg), and dimethylformamide (10 ml) was stirred at 130° C. under an atmosphere of argon for 4 hours. The mixture was evaporated and the residue was paritioned between aqueous 2M sodium hydroxide solution (10 ml) and dichloromethane (10 ml). The organic layer was separated, washed with dichloromethane (2×10 ml), dried (MgSO4) and evaporated. The residue was crystallised from acetonitrile to give 3-[2-(4-[3-pyridyl]phenyl)ethenyl]-3-hydroxyquinuclidine (400 mg) as a solid, m.p. 195°-198° C.; microanalysis, found: C, 76.4; H, 7.2; N, 8.6%; C20H22N2O.0.5H2O requires: C, 76.2; H, 7.3; N, 8.9%; NMR (DMSO-d6 +CD3COOD): 1.7-2.15(4H, m), 2.35(1H, m), 3.15-3.4(5H, m), 3.5(1H, d), 6.7(1H, d), 6.9(1H, d), 7.5-7.8(7H, m), 8.15(1H, d); m/Z 307 (M+H).

後処理

  1. customThe mixture was evaporated
  2. customThe organic layer was separated
  3. washwashed with dichloromethane (2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallised from acetonitrile

出典と根拠

ORDレコード
ord-7e48db0894324707a0c7c9d3c3b3308f
出典データセット
uspto-grants-1998_02
特許番号
US05714496

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