Hydrochloric Acid → HCID 67314373、化合物

HRID 1011335ノート

反応式

HRID 1011335 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][C:13]1[N:18]=[C:17]2[CH2:19][O:20][C:21](=O)[C:16]2=[CH:15][CH:14]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:21]1[C:16]2[C:17](=[N:18][C:13]([CH3:12])=[CH:14][CH:15]=2)[CH2:19][O:20]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 58478770HCID 58478770、化合物

生成物 1

HCID 67314373HCID 67314373、化合物収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 5-fluoro-1,3-dihydro-indol-2-one (752 mg, 4.98 mmol.) in THF (5 mL) is placed under an argon atmosphere and cooled in an ice bath. A solution of Li bis(trimethylsilyl)amide (13.2 mL of a 1M in THF, 13.2 mmol) is added slowly at 0° C. and the resulting solution is stirred at 0° C. for 10 min. The ice-bath is removed and a solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (495 mg, 3.32 mmol) in THF (6 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4.5 h and then poured into 50 mL of aqueous 10% HCl solution. After 10 min at room temperature, the reaction is heated to ˜90° C. for 45 min and is then stirred at room temperature for 36 h. The solid which precipitated from solution is collected by filtration and washed sequentially with small volumes of MeOH (3×5 mL), EtOAc (3×5 mL) and Et2O (3×5 mL) followed by drying to give the title compound as a yellow solid (450 mg, 48%).

後処理

  1. temperaturecooled in an ice bath
  2. customThe ice-bath is removed
  3. stirringThe resulting solution is stirred for 4.5 h
  4. waitAfter 10 min at room temperature
  5. temperaturethe reaction is heated to ˜90° C. for 45 min
  6. stirringis then stirred at room temperature for 36 h
  7. customThe solid which precipitated from solution
  8. filtrationis collected by filtration
  9. washwashed sequentially with small volumes of MeOH (3×5 mL), EtOAc (3×5 mL) and Et2O (3×5 mL)
  10. customby drying

出典と根拠

ORDレコード
ord-b277257833d448128debc83dab646e40
出典データセット
uspto-grants-2011_07
特許番号
US07977351B2

反応ノート

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