HCID 10318017, compound → HCID 68802893, compound

HRID 2250586Notes

Reaction equation

HRID 2250586 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:25]([CH3:27])[CH3:26])[C:9](/[CH:18]=[CH:19]/[C:20](OCC)=[O: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-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:25]([CH3:27])[CH3:26])[C:9](/[CH:18]=[CH:19]/[CH2:20][OH:21])=[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

4

Reactant 2

HCID 10318017HCID 10318017, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 68802893HCID 68802893, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of ethyl (2E)-3-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-2-propenoate (50 mg) in toluene was added dropwise 1.5 M diisobutylaluminum hydride (0.277 mL) in toluene (24 mL) in a dryice-acetone bath. After addition, the mixture was stirred for 2 hours (−10° C.). The reaction mixture was quenched with sodium, potassium-tartarate and was filtered through Celite. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash silica gel chromatography (silica gel, 40 mL) eluted with hexane-ethyl acetate=10-1, 5-1, and 3-1 to give (2E)-3-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-2-propen-1-ol as an yellow solid (30 mg).

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched with sodium, potassium-tartarate
  3. filtrationwas filtered through Celite
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash silica gel chromatography (silica gel, 40 mL)
  8. washeluted with hexane-ethyl acetate=10-1, 5-1, and 3-1

Sources & evidence

ORD record
ord-0f321df530334ef1bb6064ca39f41496
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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