Triacetoxyperiodinane → HCID 117667201, compound

HRID 712778Notes

Reaction equation

HRID 712778 reaction equation
[F:1][C:2]1[C:3]([C@@H:21]([OH:23])[CH3:22])=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:21]([C:3]1[C:2]([F:1])=[CH:7][N:6]=[CH:5][C:4]=1[C:8]1[CH:9]=[C:10]2[C:15](=[N:16][CH:17]=1)[N:14]([C:18]([NH2:20])=[O:19])[CH2:13][CH2:12][CH2:11]2)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86305760HCID 86305760, compound2×

Product 1

HCID 117667201HCID 117667201, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[5-fluoro-4-((S)-1-hydroxy-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (100 mg, 0.3 mmol, Compound 34, Example 16) in 5 mL of dichloromethane is added Dess-Martin periodinane (135 mg, 0.3 mmol, 1 eq.). The reaction is stirred at room temperature until the reaction is complete. The reaction mixture is filtered through diatomaceous earth and the filtrate is concentrated. The crude reaction product is purified by flash column chromatography to give 75 mg of the titled product.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated
  3. customThe crude reaction product
  4. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-7ed31bbde0cd4c6b8d1dc3db43d34eae
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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