Methanol → tert-butyl 4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79555ノート

反応式

HRID 79555 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:4](S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.C1COCC1.CO.[Li+].[OH-]>O>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:13][CH2:12]2)[NH:4][CH:3]=1

参加物

6

反応物 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68783101HCID 68783101、化合物

生成物 1

HCID 68761367tert-butyl 4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate収率 58.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

tert-Butyl 4-(3-methyl-5-phenyl-1-(phenyl sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.9 g, 1.69 mmol) was placed in 1:1 THF:MeOH (10 mL). 3M LiOH (aq., 5.63 mL, 16.9 mmol) was added, and the reaction was heated to 50° C. for 1 hour. The reaction was then cooled, added to water and extracted with DCM. The organics were dried, filtered and concentrated to give the crude product which was purified (500:3 to 500:8 DCM:MeOH) to give tert-butyl 4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (0.390 g, 58.8% yield).

後処理

  1. temperatureThe reaction was then cooled
  2. extractionextracted with DCM
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified (500:3 to 500:8 DCM:MeOH)

出典と根拠

ORDレコード
ord-e77c2648b0a742709b4c0a9a0345ded1
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

反応ノート

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