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

HRID 1690030ノート

反応式

HRID 1690030 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22f9639a2168401db40b2cd595877665
出典データセット
uspto-grants-2012_04
特許番号
US08153641B2

反応ノート

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