Potassium Hydroxide → 5-Fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

HRID 1690076ノート

反応式

HRID 1690076 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:5]2=[N:6][CH:7]=1.CC[C:21]([O-:23])=[O:22].[OH-].[K+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:21]([OH:23])=[O:22])[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:5]2=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 866390625-fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine 2-ethyl carboxylate

生成物 1

HCID 669079435-Fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid収率 90.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 6.9 g (20.58 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-ethyl carboxylate (WO07/010,138) and 1.89 g (33.7 mmol) of potassium hydroxide in a mixture of 80 mL of ethanol and 10 mL of water is heated under reflux for 1.5 h. After this time, the reaction mixture is concentrated at reduced pressure, and is then taken up in 200 mL of water. The solution is acidified with additions of concentrated hydrochloric acid, and then extracted three times with 50 mL of dichloromethane. The organic phases are combined, dried over sodium sulfate and then concentrated at reduced pressure. The resultant product is triturated in 5 mL of dichloromethane. A precipitate is collected by filtration and is dried at reduced pressure. In this way we isolate 5.35 g of the expected product, which is used as it is in the rest of the synthesis.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 h
  3. concentrationAfter this time, the reaction mixture is concentrated at reduced pressure
  4. extractionextracted three times with 50 mL of dichloromethane
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe resultant product is triturated in 5 mL of dichloromethane
  8. filtrationA precipitate is collected by filtration
  9. customis dried at reduced pressure

出典と根拠

ORDレコード
ord-f9b5d2a736744017b65f1e9bf3436b77
出典データセット
uspto-grants-2012_04
特許番号
US08153650B2

反応ノート

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