Water → [1,2,5]Thiadiazolo[3,4-b]pyridine-6-carbaldehyde

HRID 1943232Notes

Reaction equation

HRID 1943232 reaction equation
C1(/C=[CH:8]/[C:9]2[CH:14]=[N:13][C:12]3=[N:15][S:16][N:17]=[C:11]3[CH:10]=2)C=CC=CC=1.C[N+]1([O-])CC[O:22]CC1.O.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O.CC(C)=O>[N:17]1[S:16][N:15]=[C:12]2[C:11]=1[CH:10]=[C:9]([CH:8]=[O:22])[CH:14]=[N:13]2

Participants

8

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 685963166-[(E)-2-Phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine

Product 1

HCID 82414701[1,2,5]Thiadiazolo[3,4-b]pyridine-6-carbaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To 6-[(E)-2-phenylethenyl][1,2,5]thiadiazolo[3,4-b]pyridine (0.88 g, 3.68 mmol) was added acetone (30 ml), N-methyl-morpholine-N-oxide, 50 wt. % in water (1.525 ml, 7.35 mmol) and then osmium tetroxide in water (0.225 ml, 0.037 mmol). The reaction was then stirred for 20 hours. To the pale brown solution was added sodium periodate (3.15 g, 14.71 mmol) and stirring continued for 45 mins. The solvent was reduced by rotary evaporation and the remainder partitioned between chloroform and water. The aqueous was further extracted with chloroform and the combined organic extracts passed through a hydrophobic frit and concentrated to give brown/black solid (0.6 g). A portion of this material (0.575 g) was purified by chromatography on silica eluting with 20% EtOAc in cyclohexane to a pale yellow solid (160 mg).

Workup

  1. stirringstirring
  2. waitcontinued for 45 mins
  3. customThe solvent was reduced by rotary evaporation
  4. customthe remainder partitioned between chloroform and water
  5. extractionThe aqueous was further extracted with chloroform
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6af9bcf5f2141ba9d52ca1a3bb07de5
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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