Boron tribromide → (E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate

HRID 332899Notes

Reaction equation

HRID 332899 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[N:16][CH:17]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=3)[S:8][C:7]=2[CH:32]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[N:16][CH:17]=3)=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[S:8][C:7]=2[CH:32]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86730673HCID 86730673, compound

Product 1

HCID 136341396(E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-methyl 3-(5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate (0.096 g, 0.215 mmol) in DCM (2.145 mL) at room temperature was added BBr3 (1.0 M in heptane, 0.858 mL, 0.86 mmol) and the reaction was stirred at room temperature for 30 min. Upon completion the reaction was quenched with MeOH (2.0 mL) and stirred for 10 min at room temperature then concentrated in vacuo onto silica gel then purified by column chromatography (SiO2, 0-20% MeOH/DCM) to afford (E)-methyl 3-(5-((6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate. LC/MS (m/z, MH+): 420.3.

Workup

  1. customUpon completion the reaction was quenched with MeOH (2.0 mL)
  2. stirringstirred for 10 min at room temperature
  3. concentrationthen concentrated in vacuo onto silica gel
  4. customthen purified by column chromatography (SiO2, 0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-7161f2460b364bf1a91600f5f97d06c2
Source dataset
uspto-grants-2014_11
Patent number
US08877801B2

Reaction notes

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