Triacetoxyperiodinane → HCID 58086139, compound

HRID 1098512Notes

Reaction equation

HRID 1098512 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-2b06768382a044f384bae75930076632
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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