Triacetoxyperiodinane → Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-formyl-1H-indole-6-carboxylate

HRID 630540Notes

Reaction equation

HRID 630540 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]([F:52])=[C:29]([C:31]2[CH:32]=[N:33][C:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[C:43]([C:46]([O:48][CH3:49])=[O:47])[CH:44]=4)[C:39]([CH2:50][OH:51])=[CH:38]3)=[N:35][CH:36]=2)[CH:30]=1)[CH3:24]>ClCCl>[CH2:23]([C:25]1[CH:26]=[CH:27][C:28]([F:52])=[C:29]([C:31]2[CH:36]=[N:35][C:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[C:43]([C:46]([O:48][CH3:49])=[O:47])[CH:44]=4)[C:39]([CH:50]=[O:51])=[CH:38]3)=[N:33][CH:32]=2)[CH:30]=1)[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118676872Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(hydroxymethyl)-1H-indole-6-carboxylate

Product 1

HCID 118676844Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-formyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (0.541 g, 1.27 mmol) was added at 0° C. to a solution of 331b) (0.345 g, 0.85 mmol) in dichloromethane (25 mL). The resulting mixture was stirred at this temperature for 3 h and then filtered through celite. The filter was rinsed with dichloromethane (2×30 mL) and the filtrate was washed with saturated sodium hydrogen carbonate solution (3×20 mL) and brine (20 mL), dried over sodium sulfate and concentrated. Light yellow solid. Yield: 0.32 g (93% of theory)

Workup

  1. filtrationfiltered through celite
  2. washThe filter was rinsed with dichloromethane (2×30 mL)
  3. washthe filtrate was washed with saturated sodium hydrogen carbonate solution (3×20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f2b146793fd4800aa0d89258229ec5e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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