Ethyl Acetate → [2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]pyridin-5-yl]methanone

HRID 2293959Notes

Reaction equation

HRID 2293959 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][C:25](Cl)=[N:26][CH:27]=2)=[O:21])=[CH:5][CH:4]=1.[Na].CCO[C:33]([CH3:35])=[O:34]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][C:25]([O:34][CH2:33][CH2:35][N:26]3[CH2:27][CH2:22][CH2:23][CH2:24][CH2:25]3)=[N:26][CH:27]=2)=[O:21])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5360545Sodium2×HCID 23512898(6-Chloro-pyridin-3-yl)-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

Product 1

HCID 12992504[2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]pyridin-5-yl]methanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

[2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][2-chloropyridin-5-yl]methanone (1 g, 2.44 mmol) was dissolved in 10 mL of benzene and 950 mg (7.32 mmol) of 2-hydroxyethyl-1-piperidine was added. To the reaction mixture was added 85 mg (3.7 mmol) of sodium and the reaction was stirred at ambient temperature under a nitrogen atmosphere until all the sodium dissolved. The reaction was heated to 70° C. for two and half hours, then allowed to cool. To the reaction solution was added 150 mL of EtOAc and the solution was washed three times with saturated aqueous Na2CO3. The organic layer was separated and evaporated to dryness. The crude product was chromatographed on a silica gel column eluted with a linear gradient beginning with CHCl3 and ending with CHCl3 -MeOH (19:1). The desired fraction were determined by tlc, combined, and evaporated to dryness. This yielded the title compound as a yellow, amorphous solid.

Workup

  1. dissolutiondissolved
  2. temperatureto cool
  3. washthe solution was washed three times with saturated aqueous Na2CO3
  4. customThe organic layer was separated
  5. customevaporated to dryness
  6. customThe crude product was chromatographed on a silica gel column
  7. washeluted with a linear gradient
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-164baf96c3c04b2d87520d17505eac42
Source dataset
uspto-grants-1997_11
Patent number
US05688796

Reaction notes

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