Hydrochloric Acid → HCID 67314715、化合物

HRID 1254082ノート

反応式

HRID 1254082 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[N:17]=[C:16]2[CH2:18][O:19][C:20](=O)[C:15]2=[CH:14][CH:13]=1.Cl>C1COCC1>[CH3:11][C:12]1[N:17]=[C:16]2[CH2:18][O:19][C:20](=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[C:15]2=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 58478770HCID 58478770、化合物

生成物 1

HCID 67314715HCID 67314715、化合物収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
90 °C

実験手順

A solution of 1,3-dihydro-indol-2-one (200 mg, 1.5 mmol.) in THF (2 mL) is placed under an argon atmosphere and cooled in an ice bath. A solution of Li bis(trimethylsilyl)amide (4.0 mL of a 1M solution in THF, 4.0 mmol) is added slowly at 0° C. and the resulting solution is stirred for 10 min. The ice-bath is then removed and a solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (150 mg, 1.00 mmol) in THF (6 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h and then poured into 10% aqueous HCl solution (50 mL). After 10 min at room temperature, the reaction is heated to ˜90° C. for 45 min followed by stirring at room temperature for 36 h. The solid which precipitated from solution is collected by filtration and washed sequentially with small volumes of MeOH, EtOAc, Et2O and dried under vacuum to give the title compound as a yellow solid (78 mg, 30%).

後処理

  1. temperaturecooled in an ice bath
  2. customThe ice-bath is then removed
  3. stirringThe resulting solution is stirred for 4 h
  4. waitAfter 10 min at room temperature
  5. stirringby stirring at room temperature for 36 h
  6. customThe solid which precipitated from solution
  7. filtrationis collected by filtration
  8. washwashed sequentially with small volumes of MeOH, EtOAc, Et2O
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-8a171349c069405a98fa40c7393118cf
出典データセット
uspto-grants-2013_06
特許番号
US08455535B2

反応ノート

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