Sodium Thiosulfate → (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1690030노트

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HRID 1690030 반응식
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)[OH:12].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.O.O1CCCC1>[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)=[O:12]

참가 물질

8

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57963247(2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

생성물 1

HCID 57963249(2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone수율 83.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (37, 0.699 g, 2.42 mmol), 52 mL of tetrahydrofuran was added, followed by sodium bicarbonate (2.04 g, 24.2 mmol) and Dess-Martin periodinane (1.03 g, 2.42 mmol). The reaction was allowed to stir at room temperature for 30 minutes and 25 mL of saturated sodium thiosulfate and 30 mL of water were added, followed by 50 mL of ethyl acetate. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 20-80% ethyl acetate in hexanes (with 4% acetic acid). Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (38, 581 mg). MS (ESI) [M+H+]+=287.2.

후처리

  1. dry with materialThe organic layer was dried with magnesium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting material was purified by silica gel column chromatography
  5. washeluting with a gradient of 20-80% ethyl acetate in hexanes (with 4% acetic acid)
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-22f9639a2168401db40b2cd595877665
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153641B2

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