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Cesium carbonate → (3r)-(3-Methoxy-pyrrolidin-1-yl)-[7-(2-methyl-1h-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone

HRID 889882
ノート
印刷プレビュー

反応式

HRID 889882 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[C:15]([C:17]([N:19]3[CH2:23][CH2:22][C@@H:21]([O:24][CH3:25])[CH2:20]3)=[O:18])[S:16][C:9]=12.[CH3:26][C:27]1[NH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][C:32]([OH:36])=[CH:31][CH:30]=2>CN(C=O)C>[CH3:25][O:24][C@@H:21]1[CH2:22][CH2:23][N:19]([C:17]([C:15]2[S:16][C:9]3[C:10](=[N:11][CH:12]=[CH:13][C:8]=3[O:36][C:32]3[CH:33]=[C:34]4[C:29](=[CH:30][CH:31]=3)[NH:28][C:27]([CH3:26])=[CH:35]4)[CH:14]=2)=[O:18])[CH2:20]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

5

反応物 3

HCID 10796Cesium carbonateHCID 833362-methyl-1H-indol-5-olHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

生成物 1

HCID 10223104(3r)-(3-Methoxy-pyrrolidin-1-yl)-[7-(2-methyl-1h-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
90 °C

実験手順

Cs2CO3 (0.495 g, 1.52 mmol) was added to a solution of (3R)-(7-chloro-thieno[3,2-b]pyridin-2-yl)-(3-methoxy-pyrrolidin-1-yl)-methanone (0.228 g, 0.76 mmol) and 2-methyl-1H-indol-5-ol (0.223 9, 1.52 mmol) in DMF (5 mL), and the resulting solution was heated to 90° C. After 20 h the reaction was quenched with water, EtOAc was added, and the layers were separated. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over Na2SO4 then concentrated. The resulting material was purified on silica gel by flash column chromatography, eluting with CH2Cl2/MeOH (98/2) to afford the title compound as a white solid (0.26 g, 84%). MS: 408.8 (MH+); HPLC Rf: 5.394 min.; HPLC purity: 97%.

後処理

  1. customAfter 20 h the reaction was quenched with water, EtOAc
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationthen concentrated
  7. customThe resulting material was purified on silica gel by flash column chromatography
  8. washeluting with CH2Cl2/MeOH (98/2)

出典と根拠

ORDレコード
ord-be1de9888ff34679a55b4e1e6369b7ef
出典データセット
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06995171B2

反応ノート

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