Methyl iodide → HCID 66693093, compound

HRID 1808867Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]#[C:10][C:11]([O:13][CH3:14])=[O:12].[N-:15]=[N+:16]=[N-:17].[Na+].I[CH3:20]>O.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]([CH3:20])[N:16]=[N:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 3-(2-methoxyphenyl)propiolate (3, 932 mg, 4.90 mmol), sodium azide (478 mg, 7.35 mmol), and iodomethane (0.458 ml, 7.35 mmol) in Water (7 ml) and DMF (3 ml) was heated to 100° C. in a Microwave reactor for 6 hrs. Purified by Prep-HPLC (Varian, 15-90B in min., B=90% MeOH/10% H2O) to afford methyl 5-(2-methoxyphenyl)-1-methyl-1H-1,2,3-triazole-4-carboxylate (701 mg, 2.69 mmol, 55.0% yield), 1H-NMR (500 MHz, CD3OD), δ: 7.52-7.56 (m, 1H), 7.30 (dd, 1H), 7.12, (td, 1H), 7.06, (d, 1H), 3.90 (s, 3H), 3.86 (s, 3H), 3.82 (s, 3H). and methyl 4-(2-methoxyphenyl)-1-methyl-1H-1,2,3-triazole-5-carboxylate (185 mg, 0.711 mmol, 14.51% yield), 1H-NMR (500 MHz, CD3OD), δ: 7.49-7.46 (m, 2H), 7.10-7.07 (m, 2H), 4.32 (s, 3H), 3.79 (s, 3H), 3.78 (s, 3H).

Workup

customPurified by Prep-HPLC (Varian, 15-90B in min., B=90% MeOH/10% H2O)

Sources & evidence

ORD record: ord-bacedd9a9eed46ff8d8e1d5ef2f95e82
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362004B2

Reaction notes

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