Imidazole → HCID 11510103, compound

HRID 2059630Notes

Reaction equation

HRID 2059630 reaction equation
Br[C:2]1[O:6][C:5]2[C:7]([O:13]C(=O)C)=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:17](=[O:30])[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[N:31]1([C:2]2[O:6][C:5]3[C:7]([OH:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=3[C:3]=2[C:17](=[O:30])[C:18]2[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=2)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 11510103HCID 11510103, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan (30 mg, 0.063 mmol) and imidazole(60 mg, 0.88 mmol) in a mixture of toluene:triethylamine (3 mL: 2 drops) was refluxed for 4 hours (tlc). Solvent was distilled under vacuum and the crude residue was purified by PTLC (eluent=ethyl-acetate: 1% triethylamine) to give the title compound as a yellow solid; (8 mg, 30%); 1H NMR (300 MHz, CDCl3) δ 8.24(bs, 1H), 7.52(b, 1H), 7.19(b, 1H), 7.06(s, 2H, benzoyl Hs), 6.99(d, 1H, J=8.60 Hz), 6.93(d, 1H, J=8.66 Hz), 3.96(s, 3H, OMe), 3.91(s, 3H, OMe), 3.76(s, 6H, 2×OMe).

Workup

  1. distillationSolvent was distilled under vacuum
  2. customthe crude residue was purified by PTLC (eluent=ethyl-acetate: 1% triethylamine)

Sources & evidence

ORD record
ord-66fac87be28343509119939c4c07a49b
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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