Ethyl diazoacetate → HCID 86732054, compound

HRID 1498793Notes

Reaction equation

HRID 1498793 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])[N:11]=[C:10]([CH3:16])[CH: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:9]=[C:10]([CH3:16])[N:11]=[C:12]([C@@H:14]3[CH2:15][C@H:19]3[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=2)[N:3]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86732055HCID 86732055, compound

Product 1

HCID 86732054HCID 86732054, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyridine (24-4, 620 mg, 2.69 mmol) in toluene (12 mL) was added at reflux a solution of ethyl diazoacetate (614 mg, 5.38 mmol) in toluene (2 mL) in three portions over 10 minutes. The reaction mixture was refluxed for 2 hours, cooled to room temperature, and concentrated. The residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes) to afford ethyl trans-2-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridin-2-yl)cyclopropanecarboxylate (24-5) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.17 (d, 1H, J=1.7 Hz), 7.09 (d, 1H, J=1.7 Hz), 4.17 (q, 2H, J=7.2 Hz), 2.63-2.57 (m, 1H), 2.59 (s, 3H), 2.52 (s, 3H), 2.41 (s, 3H), 2.33-2.27 (m, 1H), 1.70-1.57 (m, 2H), 1.28 (d, 3H, J=7.2 Hz). LRMS m/z (M+H) 301 found, 301 required.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a9f2537fb95644f0a3807d08b25772b6
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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