Water → HCID 61315511, compound

HRID 2277696Notes

Reaction equation

HRID 2277696 reaction equation
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[O:20])[CH:16]=[N:17][CH:18]=1.O>C1COCC1>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]([C:8]2[N:7]([CH3:6])[CH:11]=[CH:10][N:9]=2)[OH:20])[CH:16]=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13901-MethylimidazoleHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 61315511HCID 61315511, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., under N2 protection, n-BuLi (0.16 mL, 1.6 M, 1.0 mmol) was added to a solution of 1-methyl-1H-imidazole (82 mg, 1.0 mmol) in THF (10 mL) and the reaction mixture was stirred at −78° C. for 0.5 hour; then, 5-bromo-pyridine-3-carbaldehyde (186 mg, 1.0 mmol) was added to the above solution and stirring continued at −78° C. for additional 2 hours. The reaction mixture was poured into water (5.0 mL) and extracted with EtOAc (2×50 mL). The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (210 mg, 78.4%) as white solid. MS: 268.1 & 270.1 (M+H+).

Workup

  1. stirringstirring
  2. waitcontinued at −78° C. for additional 2 hours
  3. extractionextracted with EtOAc (2×50 mL)
  4. customThe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10bc314673384e309fefdcc79025c4fe
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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