Triacetoxyperiodinane → HCID 46913049, compound

HRID 1397840Notes

Reaction equation

HRID 1397840 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([CH:12]([OH:28])[C:13]3[C:14]([F:27])=[C:15]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])=[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:27])=[C:15]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=3[F:19])=[O:28])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 70829816HCID 70829816, compound

Product 1

HCID 46913049HCID 46913049, compoundYield 57.5%

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]-2,4-difluoro-phenyl}-amide (14, 313 mg, 0.770 mmol) dissolved in 5 mL of tetrahydrofuran, Dess-Martin periodinane (327 mg, 0.770 mmol) was added as a solid. The reaction was stirred at room temperature for 1 hour, then quenched with water. The aqueous layer was 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-0002, 179 mg). MS(ESI) [M−H+]−=403.2.

Workup

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

Sources & evidence

ORD record
ord-cdf4be2c264941a1a8ff0f4a638a5438
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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