Sodium Carbonate → 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 79613

反応式

HRID 79613 の反応式
[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 602052755-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine収率 28.2%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 7.7 mmol) was placed in 6M HCl (30 mL) at room temperature. SnCl2 (7.29 g, 38.5 mmol) was then added, and the reaction was stirred for 30 minutes at room temperature. The reaction was then cooled to 0° C. and a saturated aqueous solution of Na2CO3 was added to raise the pH to 8. The reaction was then extracted with DCM (with minimal MeOH to aid solubility). The combined organic fractions were dried, filtered, and concentrated to give the crude product 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.50 g, 28.2% yield), which was used without purification.

後処理

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperatureto raise the pH to 8
  3. extractionThe reaction was then extracted with DCM (with minimal MeOH to aid solubility)
  4. customThe combined organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-262e553a27c44f969cd6bf6fe0afe17a
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

関連ノート

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