Sodium Azide → 7-Hydroxy-6-methoxy-2-(2H-tetrazol-5-yl)-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan

HRID 2059638Notes

Reaction equation

[C:1]([C:3]1[O:7][C:6]2[C:8]([O:14]C(=O)C)=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:5]=2[C:4]=1[C:18](=[O:31])[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C=O)C>[OH:14][C:8]1[C:6]2[O:7][C:3]([C:1]3[N:2]=[N:32][NH:33][N:34]=3)=[C:4]([C:18](=[O:31])[C:19]3[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=3)[C:5]=2[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

Mixture of 2-cyano-7-acetoxy-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan (15 mg, 0.04 mmol) ammonium chloride (11 mg, 0.2 mmol) and sodium azide (13 mg, 0.2 mmol) in dry DMF (400 μL) was stirred at 110° C. for 4 hours. More sodium azide (15 mg, 0.23 mmol) was added and stirring was continued for 1 hour (tlc), quenched with saturated ammonium chloride solution and extracted with ethyl-acetate (10 mL×2). The organic layer was dried over magnesium sulfate and solvent was distilled and the crude was purified by silica gel plate to afford the title compound as creamy solid; (3.5 mg, 21%; 1H NMR (300 MHz, CDCl3) δ: 7.85(1H, NH), 7.26(d, J=8.54 Hz, 1H), 7.02(s, 2H, benzoyl Hs), 6.95(d, J=8.54 Hz, 1H), 5.74(b, 1H, OH), 3.97(s, 3H, OMe), 3.88(s, 3H, OMe), 3.82(s, 6H, 2×OMe).

Workup

stirringstirring
waitwas continued for 1 hour
custom(tlc), quenched with saturated ammonium chloride solution
extractionextracted with ethyl-acetate (10 mL×2)
dry with materialThe organic layer was dried over magnesium sulfate and solvent
distillationwas distilled
customthe crude was purified by silica gel plate

Sources & evidence

ORD record: ord-f8e87ddc09dd40eb879b9b6d3b69055e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278290B2

Reaction notes

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