1H-1,2,4-Triazole → HCID 11524689, compound

HRID 1042597Notes

Reaction equation

HRID 1042597 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[C:9]1[O:13][C:12]2[C:14]([O:20]C(=O)C)=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=2[C:10]=1[C:24](=[O:37])[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1>O1CCCC1.C1(C)C=CC=CC=1>[N:1]1([C:9]2[O:13][C:12]3[C:14]([OH:20])=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:24](=[O:37])[C:25]2[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 11524689HCID 11524689, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,4-triazole (22 mg, 0.32 mmol) in dry tetrahydrofuran (2 mL) was added sodium hydride (60%, 24 mg, 0.60 mmol) and resulting suspension was treated with a solution of 2-bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan (50 mg, 0.10 mmol) in dry toluene (2 mL). The mixture was stirred at reflux for 6 hours (tlc), quenched with saturated ammonium chloride solution, extracted with dichloromethane (10 mL), dried over magnesium sulphate and the solvent distilled under vacuum. The crude residue was purified by PTLC (eluent=ethyl acetate: 1% triethylamine) to give the title compound as a yellow solid; (22 mg, 50%); 1H NMR (300 MHz, CDCl3) δ 8.64 (bs, 1H), 8.06 (bs, 1H), 7.10 (d, 1H, J=8.60 Hz), 7.05 (s, 2H, benzoyl Hs), 6.98 (d, 1H, J=8.65 Hz), 3.98 (s, 3H, OMe), 3.89 (s, 3H, OMe), 3.77 (s, 6H, 2×OMe).

Workup

  1. customresulting suspension
  2. temperatureat reflux for 6 hours (tlc)
  3. customquenched with saturated ammonium chloride solution
  4. extractionextracted with dichloromethane (10 mL)
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent distilled under vacuum
  7. customThe crude residue was purified by PTLC (eluent=ethyl acetate: 1% triethylamine)

Sources & evidence

ORD record
ord-5e10ee1d6bb64090b57661133bcf0968
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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