Triacetoxyperiodinane → HCID 58086452, compound

HRID 253425Notes

Reaction equation

HRID 253425 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C:8]2[C:9]([O:25][CH2:26][CH2:27][F:28])=[C:10]([CH:14]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[OH:15])[CH:11]=[CH:12][CH:13]=2)=[C:4]([F:31])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C:8]2[C:9]([O:25][CH2:26][CH2:27][F:28])=[C:10]([C:14]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[O:15])[CH:11]=[CH:12][CH:13]=2)=[C:4]([F:31])[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58087155HCID 58087155, compound

Product 1

HCID 58086452HCID 58086452, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(4-chloro-2-fluoro-benzyloxy)-2-(2-fluoro-ethoxy)-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (95, 60 mg, 0.1 mmol) in tetrahydrofuran (10 mL) was added Dess-Martin periodinane (69 mg, 0.16 mmol) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The reaction was quenched with a saturated solution of sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexanes to provide the compound as a white solid (P-2086, 15 mg, 20%). MS (ESI) [M+H+]+=441.06.

Workup

  1. customThe reaction was quenched with a saturated solution of sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0fe75e6971c74d6ebdf0b5de73cd543b
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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