Hydrochloric Acid → HCID 59612972, compound

HRID 445643Notes

Reaction equation

HRID 445643 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](N)[C:5]([CH3:8])=[N:6][CH:7]=1.Cl.[O:11]1[CH2:16][CH2:15]OCC1.N(O[CH2:20]CC(C)C)=O>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH:16]([CH3:20])[CH3:15])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 312751,4-DioxaneHCID 219640965-Bromo-2-methylpyridin-3-amine

Product 1

HCID 59612972HCID 59612972, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-methyl-pyridin-3-ylamine (Stage 75.1.4, 400 mg, 2.13 mmol) in isopropanol (33 ml) were added 4 M HCl in dioxane (0.535 ml, 2.13 mmol) and isoamyl nitrite (1.25 g, 10.7 mmol). The reaction mixture was heated at 80° C. for 2.5 h, before being evaporated to dryness. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was dry loaded on silica gel and purified by MPLC (heptane/EtOAc 0% to 30%) to give the title compound as an orange oil (HPLC: tR 2.47 min (Method A); M+H=230, 232 MS-ES).

Workup

  1. custombefore being evaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was dry
  9. custompurified by MPLC (heptane/EtOAc 0% to 30%)

Sources & evidence

ORD record
ord-1d8d0eaad5da49ed9cab045d35329543
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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