1-Butanol → HCID 86664931, compound

HRID 1256232Notes

Reaction equation

HRID 1256232 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([CH:19]=C)[CH:15]=[CH:14][C:13]=2[C:12]2[N:21]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:22]=[CH:23][C:11]=2[N:10]=1.O.C([OH:35])CCC.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([CH:19]=[O:35])[CH:15]=[CH:14][C:13]=2[C:12]2[N:21]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:22]=[CH:23][C:11]=2[N:10]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 962Water2×HCID 23667635Sodium periodateHCID 67494412HCID 67494412, compound

Product 1

HCID 86664931HCID 86664931, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 250 ml round-bottomed flask equipped with a magnetic stirrer and with a septum having a top-mounted argon intake is charged with 2.36 g of 5-(2,6-difluorophenyl)-7-ethenyl-N,N-dimethyl-1H-pyrazolo[4,3-c]isoquinoline-1-sulphonamide in 30 ml of THF and then 23 ml of water, 30 ml of tort-butanol, 2.14 ml of a solution of osmium tetroxide at 2.5% in 2-methyl-2-propanol, and 5.04 g of sodium periodate are added. The mixture is stirred at RT for 4 h and then poured into 100 ml of water and extracted with AcOEt. The organic phase is washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated under RP. The crude product is purified by chromatography on silica gel (15-40 μm), eluting with DCM, to give 1.92 g of 5-(2,6-difluorophenyl)-7-formyl-N,N-dimethyl-1H-pyrazolo[4,3-c]isoquinoline-1-sulphonamide (beige solid). LC-MS-DAD-ELSD: 417 (+)=(M+H)(+).

Workup

  1. customA 250 ml round-bottomed flask equipped with a magnetic stirrer and with a septum
  2. extractionextracted with AcOEt
  3. washThe organic phase is washed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under RP
  7. customThe crude product is purified by chromatography on silica gel (15-40 μm)
  8. washeluting with DCM

Sources & evidence

ORD record
ord-aa91fdeb714f442498851b871b2f00d3
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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