Sodium Methoxide → HCID 68291481, compound

HRID 1507937Notes

Reaction equation

HRID 1507937 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[CH3:15][O-:16].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([O:16][CH3:15])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291481HCID 68291481, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 285 mg, 1.038 mmol), sodium methoxide (1.402 mL, 5.19 mmol) in MeOH (5 mL) was stirred at rt for 3 days. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated to afford a yellow solid that was chromatographed on a 24 gm silica gel cartridge, eluting with a 0-100% EtOAc/hexanes gradient. Fractions containing the product were concentrated to afford the title compound (112 mg, 0.405 mmol, 39.0% yield) as a yellow solid. HPLC (condition M): retention time=1.70 min.; LCMS (ES+) m/z: 271.9 (bromine pattern); H 1NMR (400 MHz, CDCl3) δ ppm 4.44 (s, 3 H), 5.71 (brs, 1 H), 6.99 (d, J=1.8 Hz, 1 H), 7.22 (brs, 1 H), 7.81 (d, J=1.8 Hz, 1 H), 8.69 (s, 1 H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between EtOAc (50 ml) and water (50 ml)
  3. washThe organic layer was washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford a yellow solid
  7. customthat was chromatographed on a 24 gm silica gel cartridge
  8. washeluting with a 0-100% EtOAc/hexanes gradient
  9. additionFractions containing the product
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-220e1b4df16c4cb9bf688fcd14174055
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

Loading…