Triacetoxyperiodinane → HCID 59565387, compound

HRID 1892054Notes

Reaction equation

HRID 1892054 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]([CH2:22][OH:23])([CH3:21])[C:19]#[CH:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]([CH:22]=[O:23])([CH3:21])[C:19]#[CH:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 595653502-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide

Product 1

HCID 59565387HCID 59565387, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide (0.513 g) in dichloromethane (25 ml) was treated with Dess-Martin periodinane (0.737 g). The reaction mixture was stirred at room temperature for 2 hrs and then, quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The reaction mixture was vigorously stirred at rt. for 40 minutes after which time the two phases were separated. The organic layer was washed thrice with sat. aqueous. NaHCO3. After separation, the organic phase was dried over sodium sulphate, filtered and evaporated to yield 0.523 g of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-formyl-1-methyl-prop-2-ynyl)-2-methylsulfanyl acetamide as a crude product along with minor impurities. The crude mixture was used in the next step without any further purification.

Workup

  1. customquenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate
  2. stirringThe reaction mixture was vigorously stirred at rt
  3. customfor 40 minutes after which time the two phases were separated
  4. washThe organic layer was washed thrice with sat. aqueous
  5. customAfter separation
  6. dry with materialthe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-064c148951d44e289d0bb2dd9fa96eda
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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