Chlorosuccinimide → HCID 90775215, compound

HRID 2250578Notes

Reaction equation

HRID 2250578 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:11]([CH3:12])=[N:10][N:9]2[CH:13]=[CH:14][CH:15]=[C:8]2[C:7]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH3:2].[Cl:24]N1C(=O)CCC1=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[C:11]([CH3:12])=[N:10][N:9]2[C:13]([Cl:24])=[CH:14][CH:15]=[C:8]2[C:7]=1[C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 91147555Ethyl[4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate

Product 1

HCID 90775215HCID 90775215, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl[4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate (100 mg) in tetrahydrofuran (2 ml) was added N-chlorosuccinimide (43 mg) and the mixture was stirred at 20° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with aqueous ethyl acetate, water and brine, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography eluting with a mixture of toluene and ethyl acetate (10:1) to give ethyl[7-chloro-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate (34 mg) as an yellow oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with aqueous ethyl acetate, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of toluene and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-515acee7f91d452a95e8a7417fa8868f
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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