p-Toluenesulfonic acid → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid

HRID 2367697ノート

反応式

HRID 2367697 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([OH:13])=[O:12].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[N:6]=[C:5]2[C:11]([OH:13])=[O:12]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acid2 回HCID 80803,4-dihydro-2H-pyran2 回HCID 71573585-bromo-1H-indazole-3-carboxylic Acid

生成物 1

HCID 698056555-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid収率 60.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-bromo-1H-indazole-3-carboxylic acid (CXV) (59.8 g, 248 mmol) in THF (800 mL) under argon was added 3,4 dihydro-2H-pyran (50.6 mL, 558 mmol) and p-TsOH (4.72 g, 24.8 mmol). The reaction was heated to reflux at 60° C. for 16 h. An additional portion of p-TsOH (0.025 eq) and 3,4 dihydro-2H-pyran (0.56 eq) was added and the reflux continued for 5 h. The solution was concentrated under vacuum. EtOAc was added to the residue and the suspension was filtered and dried under high vacuum overnight to produce 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid (CXVIII) as a white solid (49.07 g, 150.9 mmol, 60.8% yield). ESIMS found for C13H13BrN2O3 m/z 326.3 (M+H).

後処理

  1. temperatureThe reaction was heated
  2. concentrationThe solution was concentrated under vacuum
  3. additionEtOAc was added to the residue
  4. filtrationthe suspension was filtered
  5. customdried under high vacuum overnight

出典と根拠

ORDレコード
ord-4dd9615f77334af897f54dd3fd46a5da
出典データセット
uspto-grants-2014_04
特許番号
US08697887B2

反応ノート

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