Pyridazine → HCID 86730395, compound

HRID 871136Notes

Reaction equation

HRID 871136 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.[Br:7][C:8]1[C:9]([F:16])=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].[Li]N1C(C)(C)CCCC1(C)C.Cl.CCO.C1COCC1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:7][C:8]1[C:9]([F:16])=[C:10]([CH:11]([C:6]2[N:1]=[N:2][CH:3]=[CH:4][CH:5]=2)[OH:12])[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 9259PyridazineHCID 516892Sodium BicarbonateHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 23103637HCID 23103637, compoundHCID 178418821HCID 178418821, compound

Product 1

HCID 86730395HCID 86730395, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of pyridazine (0.078 mL, 1.075 mmol) in THF (2.0 mL) and a solution of 3-bromo-2-fluorobenzaldehyde (0.200 g, 0.985 mmol) in THF (2.0 mL) were added simultaneously to a cold solution of LTMP at −78° C. The mixture was stirred at −78° C. for 4 h, followed by the addition of excess of HCl/EtOH/THF. The solution was allowed to warm to room temperature, then treated with a saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (3×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound (0.254 g, 0.897 mmol, 100% yield) as a yellow residue.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b79fa29afa7e49728be84dc058cc0f2b
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

Loading…