Triacetoxyperiodinane → HCID 58086139, compound

HRID 1261152Notes

Reaction equation

HRID 1261152 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-77cdca7b662f4e0ca28bbe4c9bfdb436
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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