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

HRID 1965024Notes

Reaction equation

HRID 1965024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([OH:26])[C:12]3[CH:13]=[C:14]([NH:19][S:20]([CH2:23][CH2:24][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[CH:13]=[C:14]([NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=3[F:18])=[O:26])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58086451Propane-1-sulfonic acid 3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-4-fluoro-phenyl-amide

Product 1

HCID 58086469Propane-1-sulfonic acid [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-4-fluoro-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid 3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-4-fluoro-phenyl-amide (673, 55.0 mg, 0.12 mmol) in tetrahydrofuran (8.0 mL) was added Dess-Martin periodinane (70.0 mg, 0.17 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was concentrated with silica gel and purified with silica gel column chromatography eluting with 25% ethyl acetate in hexane to give an off-white solid (P-1403, 26.2 mg, 47%). MS (ESI) [M+H+]+=437.9, 439.9.

Workup

  1. concentrationThe reaction was concentrated with silica gel
  2. custompurified with silica gel column chromatography
  3. washeluting with 25% ethyl acetate in hexane
  4. customto give an off-white solid (P-1403, 26.2 mg, 47%)

Sources & evidence

ORD record
ord-49a8ded1e54b4493aa3ec3a92f5ce189
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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