Triacetoxyperiodinane → HCID 58565349, compound

HRID 2175316Notes

Reaction equation

HRID 2175316 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[C:29]([CH2:40][OH:41])[N:30]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[C:29]([CH:40]=[O:41])[N:30]2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58565373HCID 58565373, compound

Product 1

HCID 58565349HCID 58565349, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodinane (1.3 g, 2.9 mmol) was added to a solution of [6-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]methanol (0.53 g, 1.9 mmol) in methylene chloride (10 mL). The solution was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane, washed with 1:1 aqueous saturated Na2S2O3 and NaHCO3. The organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0-20% EtOAc in hexane) to give the desired product (50 mg). LCMS calculated for C15H10ClFNO(M+H)+: m/z=274.0. Found: 274.0.

Workup

  1. washwashed with 1:1 aqueous saturated Na2S2O3 and NaHCO3
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-823727c8f31845a28d1e9fb9d1659998
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

Loading…