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Potassium Carbonate → [5-(1-Benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(2,6-dimethoxy-pyridin-3-ylmethyl)-amine

HRID 509970
ノート
印刷プレビュー

反応式

HRID 509970 の反応式
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][O:29][C:30]1[C:35]([CH:36]=O)=[CH:34][CH:33]=[C:32]([O:38][CH3:39])[N:31]=1.C([BH3-])#N.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(O)(=O)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH:27][CH2:36][C:35]4[C:30]([O:29][CH3:28])=[N:31][C:32]([O:38][CH3:39])=[CH:33][CH:34]=4)=[N:25][CH:26]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 498716Cyano-borohydrideHCID 122692112,6-Dimethoxypyridine-3-carboxaldehydeHCID 576192232-Pyridinamine, 5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-

生成物 1

HCID 67199355[5-(1-Benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(2,6-dimethoxy-pyridin-3-ylmethyl)-amine
収率 72.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To 5-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (120, 60.0 mg, 0.150 mmol) in 2.0 mL of ethanol and 0.1 mL of acetic acid, 2,6-dimethoxy-pyridine-3-carbaldehyde (121, 120 mg, 0.75 mmol) and silica supported cyanoborohydride (0.40 g, 0.484 mmol) were added. The reaction was heated to 100° C. for 18 minutes at 300 Watts in microwave, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (122, 60 mg).

後処理

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-3de161489d814067bfa75b096c9b7778
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096593B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート