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

HRID 509960

反応式

HRID 509960 の反応式
[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

参加物

4

反応物 2

HCID 15847209sodium thiosulfite anhydrousHCID 58259120HCID 58259120、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-510c1f871672421eba91ddc709628ff1
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

関連ノート

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