Triacetoxyperiodinane → HCID 68502134, compound

HRID 2381080Notes

Reaction equation

HRID 2381080 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[F:23][C:24]([F:42])([F:41])[C:25]1[N:29]2[N:30]=[C:31]([N:34]3[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]3)[CH2:32][CH2:33][C:28]2=[N:27][N:26]=1>C(Cl)Cl>[F:42][C:24]([F:23])([F:41])[C:25]1[N:29]2[N:30]=[C:31]([N:34]3[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][CH2:35]3)[CH2:32][CH2:33][C:28]2=[N:27][N:26]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68499637HCID 68499637, compound

Product 1

HCID 68502134HCID 68502134, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (3.52 g, 8.30 mmol) was added to 1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (2.0 g, 6.91 mmol) in DCM (30 mL). The resulting suspension was stirred at ambient temperature for 90 minutes. The reaction mixture was diluted with DCM (300 mL) and washed with 2M NaOH (2×200 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to give 1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one (0.640 g, 32%) as a solid.

Workup

  1. washwashed with 2M NaOH (2×200 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 5 to 10% MeOH in DCM
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-a022778060d441ce828acdde099b5b26
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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