Triacetoxyperiodinane → HCID 58086139, compound

HRID 1964998Notes

Reaction equation

HRID 1964998 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([Br:25])[CH:23]=3)[NH:18][CH:17]=2)[OH:15])[CH:7]=[C:8]([O:10][CH:11]([F:13])[F:12])[CH:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[F:13][CH:11]([F:12])[O:10][C:8]1[CH:7]=[C:6]([C:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([Br:25])[CH:23]=3)[NH:18][CH:17]=2)=[O:15])[CH:5]=[C:4]([O:3][CH:2]([F:26])[F:1])[CH:9]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58087116HCID 58087116, compound

Product 1

HCID 58086139HCID 58086139, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (3,5-Bis-difluoromethoxy-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (530, 70.0 mg, 0.16 mmol) in tetrahydrofuran (6.0 mL) was added Dess-Martin periodinane (75.0 mg, 0.18 mmol). The reaction was stirred at room temperature for 10 minutes. The reaction mixture was concentrated with silica gel and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound as a white solid (P-1519, 65.0 mg, 93%.). MS (ESI) [M−H+]−=431.0, 433.0.

Workup

  1. concentrationThe reaction mixture was concentrated with silica gel
  2. custompurified with silica gel column chromatography
  3. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-103028e850674a55a901dd674a0eba77
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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