Dimethyl acetylenedicarboxylate → Trimethyl 2-methoxypyrrolo[1,2-b]pyridazine-5,6,7-tricarboxylate

HRID 1748193Notes

Reaction equation

HRID 1748193 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:9][O:10][C:11]([C:13]#[C:14][C:15]([O:17][CH3:18])=[O:16])=[O:12]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[N:5]([C:13]([C:11]([O:10][CH3:9])=[O:12])=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:13]=2[C:11]([O:10][CH3:9])=[O:12])[N:4]=1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 2924933-Methoxypyridazine

Product 1

HCID 67985277Trimethyl 2-methoxypyrrolo[1,2-b]pyridazine-5,6,7-tricarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available 3-methoxypyridazine (3.00 g, 27.3 mmol) was dissolved in methanol (60 mL) and cooled to 0° C. Dimethylacetylene dicarboxylate (4.00 mL, 32.8 mmol, 1.2 eq) was added dropwise while the reaction was rapidly stirred. The mixture was maintained at −20° C. for two days. A pale yellow solid formed during this time that was recovered by filtration and washed with cold methanol (2 mL) to furnish an off white solid. MS m/z 323.1 (M+1).

Workup

  1. temperatureThe mixture was maintained at −20° C. for two days
  2. customA pale yellow solid formed during this time that
  3. filtrationwas recovered by filtration
  4. washwashed with cold methanol (2 mL)
  5. customto furnish an off white solid

Sources & evidence

ORD record
ord-71cfff5a226b4c3fa9868f337aabf705
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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