sodium thiosulfite anhydrous → 6-[(5-Fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde

HRID 509960

Reaction equation

HRID 509960 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[N:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.S([O-])([O-])=S.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[N:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 15847209sodium thiosulfite anhydrousHCID 58259120HCID 58259120, compound

Product 1

HCID 866533266-[(5-Fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To {6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanol (92, 0.353 g, 1.34 mmol) dissolved in 8 mL of tetrahydrofuran, Dess-Maritn periodinane (0.626 g, 1.47 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was poured into aqueous saturated sodium thiosulfite and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=262.3.

Workup

  1. additionDess-Maritn periodinane (0.626 g, 1.47 mmol) was added
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-510c1f871672421eba91ddc709628ff1
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Linked notes

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