Potassium Carbonate → 5-ethynyl-1-methyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

HRID 1055016Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[C:14](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:7]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=1)#[CH:14]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred mixture of 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (1.57 g, 8.71 mmol, Eq: 1.00) and potassium carbonate (2.41 g, 17.4 mmol, Eq: 2) at 25° C. in methanol (60 ml) under an argon atmosphere was added dropwise a solution of dimethyl 1-diazo-2-oxopropylphosphonate (2.01 g, 1.57 ml, 10.5 mmol, Eq: 1.2) in methanol (12 ml). The mixture was stirred at 25° C. for 3 h. The crude material was applied on silica gel and purified by flash chromatography over a 50 g silica gel column using dichloromethane/methanol 0-10% as eluent affording 5-ethynyl-1-methyl-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (785 mg, 51.1%) as an orange solid. MS: m/z=149.2 (M+H+)

Workup

custompurified by flash chromatography over a 50 g silica gel column

Sources & evidence

ORD record: ord-5a724fb60f8648e8877f430908bfb11f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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