Triacetoxyperiodinane → HCID 59224306, compound

HRID 1869216Notes

Reaction equation

HRID 1869216 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([CH:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:35][CH2:36][OH:37])[CH:32]=[CH:33][C:26]=12.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([CH:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:35][CH:36]=[O:37])[CH:32]=[CH:33][C:26]=12

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57985934HCID 57985934, compound

Product 1

HCID 59224306HCID 59224306, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a RT mixture of Dess-Martin periodane (1.69 g, 3.99 mmol) in DCM (50 mL) was added 3-(4-methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propan-1-ol (563 mg, 2.0 mmol). The reaction was stirred at RT for 2 h and then poured in a saturated solution of NaHCO3. The organic layer was separated, and the aqueous was extracted with a mixture DCM/EtOAc (2/1). The combined organic layers were dried over MgSO4, filtered and concentrated to give 3-(4-Methoxy-pyrrolo[2,3-b]pyridin-1-yl)-3-phenyl-propionaldeyde, which was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with a mixture DCM/EtOAc (2/1)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5704c5e25a854e8881c7ce9fd6af1274
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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