Water → HCID 46909735, compound

HRID 1091906Notes

Reaction equation

HRID 1091906 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([OH:35])[C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])[C:4]=12)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([C:12]([C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=3[F:19])=[O:35])[C:4]=12)#[CH:2]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 59487255HCID 59487255, compound

Product 1

HCID 46909735HCID 46909735, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-{3-[(4-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide (8, 0.146 g, 0.288 mmol) dissolved in 15 mL of tetrahydrofuran, Dess-Martin periodinane (0.122 g, 0.288 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer separated and washed with brine, then dried over magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the resulting material was purified by silica gel column chromatography, eluting with 0 to 30% ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum, and this material was further purified by silica gel column chromatography, eluting with 0 to 15% ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-0001, 121 mg). MS (ESI) [M+H+]+=506.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe resulting material was purified by silica gel column chromatography
  8. washeluting with 0 to 30% ethyl acetate and hexane
  9. customthe solvent removed under vacuum
  10. customthis material was further purified by silica gel column chromatography
  11. washeluting with 0 to 15% ethyl acetate and hexane
  12. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-e9c09e781e37423399f98f2bb9562331
Source dataset
uspto-grants-2012_03
Patent number
US08129404B2

Reaction notes

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