Triacetoxyperiodinane → isobutane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-amide

HRID 217618Notes

Reaction equation

HRID 217618 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([OH:28])[C:12]3[C:13]([F:27])=[C:14]([NH:19][S:20]([CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([C:12]3[C:13]([F:27])=[C:14]([NH:19][S:20]([CH2:23][CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=3[F:18])=[O:28])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 595695972-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide

Product 1

HCID 59569619isobutane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-amideYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottom flask, 2-methyl-propane-1-sulfonic acid {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide (68, 618 mg, 1.30 mmol) was dissolved in 20 mL of tetrahydrofuran, and Dess-Martin periodinane (555 mg, 1.31 mmol) was added. The reaction was stirred at room temperature for 30 minutes, then quenched with water and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate, water, and brine, then dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with dichloromethane and methanol. Appropriate fractions were collected and concentrated under vacuum to provide the desired compound (69, 257 mg). MS (ESI) [M−H+]−=469.9, 471.9.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with sodium bicarbonate, water, and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with dichloromethane and methanol
  9. customAppropriate fractions were collected
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b6f942ea4404409891e5b78b28c9dece
Source dataset
uspto-grants-2012_06
Patent number
US08198273B2

Reaction notes

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