Triacetoxyperiodinane → HCID 86634740, compound

HRID 911001Notes

Reaction equation

HRID 911001 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.CCOCC.[OH-].[Na+]>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([CH:11]=[CH:10][N:9]=2)[CH:14]=[O:15])[S:5][CH:6]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57419934HCID 57419934, compound

Product 1

HCID 86634740HCID 86634740, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of (2-(4-methylthiazol-2-ylamino)pyridin-4-yl)methanol (0.210 g, 0.949 mmol) in THF (5 mL) was added to a solution of Dess-Martin periodinane (0.604 g, 1.42 mmol) in THF (5 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 30 minutes, then diluted with ether and 1N NaOH (40 mL). The reaction mixture was stirred for 30 minutes, then extracted with ether, washed with water, brine, dried and concentrated to afford 2-(4-methylthiazol-2-ylamino)isonicotinaldehyde (0.197 g, 94.7% yield) as a yellow wax/powder. The crude product was used in the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42df754610e248b0a089f945ee0a385b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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