Triacetoxyperiodinane → HCID 58086109, compound

HRID 250624Notes

Reaction equation

HRID 250624 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([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:10][C:9]=2[F:25])=[CH:4][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:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([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:10][C:9]=2[F:25])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58086104[4-(4-chloro-benzyloxy)-3-fluoro-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Product 1

HCID 58086109HCID 58086109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [4-(4-chloro-benzyloxy)-3-fluoro-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (P-1895, 17.7 mg, 0.046 mmol) in tetrahydrofuran (10.0 mL) was added Dess-Martin periodinane (23.5 mg, 0.056 mmol). The reaction was stirred at room temperature for 15 minutes. The reaction was concentrated, then purified with silica gel column chromatography eluting with 50% ethyl acetate in hexane to give a white solid (P-1897, 6.4 mg, 36.3%). MS (ESI) [M+H4]+=381.3.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified with silica gel column chromatography
  3. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3f092829627745f8a9ecd4a6c0421e60
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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