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

HRID 509960

반응식

HRID 509960 반응식
[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

참가 물질

4

반응물 2

HCID 15847209sodium thiosulfite anhydrousHCID 58259120HCID 58259120, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-510c1f871672421eba91ddc709628ff1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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