Ethyl diazoacetate → HCID 86732060, compound

HRID 1498796Notes

Reaction equation

HRID 1498796 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([CH:14]=[CH2:15])[CH:11]=[C:10]([CH3:16])[N:9]=2)[N:3]=1.[N+](=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N-]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:15][C@H:19]3[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=[C:10]([CH3:16])[N:9]=2)[N:3]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86732058HCID 86732058, compound

Product 1

HCID 86732060HCID 86732060, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methyl-4-vinylpyridine (25-1) (200 mg, 0.933 mmol) in toluene (8 mL) was added at reflux ethyl diazoacetate (852 mg, 7.47 mmol) in three portions over 4 hours. The mixture was refluxed for another 2 hours, cooled to room temperature, and concentrated. The residue was purified by silica gel column chromatography (0-70% ethyl acetate in hexanes) to give ethyl trans-2-(2-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-4-yl)cyclopropanecarboxylate (25-2) as a yellow oil. 1H NMR (300 MHz, CDCl3) 57.32 (br s, 1H), 6.83 (br s, 1H), 4.18 (q, 2H, J=7.2 Hz), 2.80 (s, 3H), 2.55-2.46 (m, 1H), 2.51 (s, 3H), 2.41 (s, 3H), 2.09-1.99 (m, 1H), 1.73-1.63 (m, 1H), 1.46-1.36 (m, 1H), 1.28 (t, 1H, J=7.2 Hz). LRMS m/z (M+H) 301 found, 301 required.

Workup

  1. temperatureThe mixture was refluxed for another 2 hours
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (0-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6b599af8ba714daca89b515c4d7c7eb9
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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