Boron Trichloride → [2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]pyridin-5-yl]methanone

HRID 2293958Notes

Reaction equation

HRID 2293958 reaction equation
C[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]C)[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[N:26][CH:27]=2)=[O:21])=[CH:5][CH:4]=1.B(Cl)(Cl)Cl>ClC(Cl)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[N:26][CH:27]=2)=[O:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 12992504[2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]pyridin-5-yl]methanone

Product 1

HCID 9891059[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]pyridin-5-yl]methanone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

[2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][2-[2-(1-piperidinyl)ethoxy]-pyridin-5-yl]methanone (1.8 g, 3.58 mmol) of was dissolved in 20 mL of dichloroethane and 3.1 mL (35.8 mmol) of condensed BCl3 was added. The reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for forty-eight hours. The reaction was quenched with 5 mL of MeOH and reaction was stirred for one hour. The reaction volume was evaporated to half the orginal volume and chromatographed on a silica gel column eluted with a linear gradient starting with CHCl3 and ending with CHCl3 -MeOH (9:1) (v/v). The desired fractions were determined by tlc, combined, and evaporated to dryness. The crude product was again chromatographed on a silica gel column eluted with CHCl3 -MeOH (19:1). This yielded 540 mg of the title compound as a yellow-orange, amorphous solid.

Workup

  1. additionwas added
  2. customThe reaction was quenched with 5 mL of MeOH and reaction
  3. stirringwas stirred for one hour
  4. customThe reaction volume was evaporated to half the orginal volume
  5. customchromatographed on a silica gel column
  6. washeluted with a linear gradient
  7. customevaporated to dryness
  8. customThe crude product was again chromatographed on a silica gel column
  9. washeluted with CHCl3 -MeOH (19:1)

Sources & evidence

ORD record
ord-f68d1d7fb0214f69a6f1922888132b22
Source dataset
uspto-grants-1997_11
Patent number
US05688796

Reaction notes

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