Methyl iodide → HCID 69306942, compound

HRID 860445Notes

Reaction equation

HRID 860445 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:22]([CH3:24])[CH3:23])[C:9](/[CH:18]=[CH:19]/[CH2:20][OH:21])=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[CH3:27]I>CN(C)C=O>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:22]([CH3:24])[CH3:23])[C:9](/[CH:18]=[CH:19]/[CH2:20][O:21][CH3:27])=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68802893HCID 68802893, compound

Product 1

HCID 69306942HCID 69306942, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-3-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-2-propen-1-ol (30 mg) in N,N-dimethylformamide (1 mL) was added 60% sodium hydride in oil (3.8 mg) in an ice-water bath under nitrogen atmosphere. After 20 minutes, to the mixture was added methyl iodide (18.5 mg) at the temperature. After 15 minutes, the reaction mixture was stirred at ambient temperature for 5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water three times and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=10-1) to give 7-chloro-4-(4-fluorophenyl)-2-isopropyl-3-[(1E)-3-methoxy-1-propenyl]pyrrolo[1,2-b]pyridazine as a brown oil (3.5 mg, 10.2%).

Workup

  1. waitAfter 15 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water three times and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by p-TLC (hexane-ethyl acetate=10-1)

Sources & evidence

ORD record
ord-ee246a12a07a408589ad53a119198d1f
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

Loading…