Triacetoxyperiodinane → HCID 46913050, compound

HRID 1397849Notes

Reaction equation

HRID 1397849 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([CH:12]([OH:27])[C:13]3[C:14]([F:26])=[C:15]([NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([C:12]([C:13]3[C:14]([F:26])=[C:15]([NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22])[CH:16]=[CH:17][CH:18]=3)=[O:27])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86647372HCID 86647372, compound

Product 1

HCID 46913050HCID 46913050, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid {3-[(5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2-fluoro-phenyl}-amide (23, 77 mg, 0.20 mmol) dissolved in 1 mL of tetrahydrofuran, Dess-Martin periodinane (92.5 mg, 0.218 mmol) was added as a solid. The reaction was stirred at room temperature for 1 hour, then quenched with water. The aqueous layer was separated and extracted with ethyl acetate, and the organice layers combined, washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated under vacuum and the resulting residue was purified by silica gel column chromatography eluting with ethyl acetate and hexanes to provide the desired compound (P-0003, 67 mg). MS(ESI) [M−H+]−=385.4.

Workup

  1. customquenched with water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum
  8. customthe resulting residue was purified by silica gel column chromatography
  9. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-37615d1d43d94c91acf1bd3d02d5f6a3
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

Loading…