Sodium Thiosulfate → HCID 46893932, compound

HRID 1091904Notes

Reaction equation

HRID 1091904 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)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>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:31])[F:32])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])=[O:35])[C:4]=12)#[N:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59487256N-{3-[(4-Cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 46893932HCID 46893932, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-{3-[(4-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide (6, 15 mg, 0.030 mmol) dissolved in 0.2 mL of tetrahydrofuran, Dess-Martin periodinane (13.8 mg, 0.0324 mmol) was added. The reaction mixture was stirred at room temperature for one hour. The reaction mixture was poured into saturated sodium thiosulfate, the organic layer separated and washed with brine, then dried over sodium sulfate and filtered. The filtrate was concentrated under vacuum and the resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-0001, 4 mg). MS (ESI) [M−H+]−=505.5.

Workup

  1. customthe organic layer separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe resulting material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate and hexane
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0f8bfd02770a45f4901c255c115ec3a6
Source dataset
uspto-grants-2012_03
Patent number
US08129404B2

Reaction notes

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