Cesium carbonate → 2-Bromo-11-fluoro-5,6-dihydroindolo[2,1-f][1,6]naphthyridine

HRID 595682ノート

反応式

HRID 595682 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[C:17]([F:20])[CH:16]=[CH:15][CH:14]=3)[C:5]([CH2:8][CH2:9]Cl)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[CH2:8][CH2:9][N:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[C:17]([F:20])[C:18]=4[CH:19]=[C:11]3[C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 10796Cesium carbonateHCID 903335962-(5-bromo-2-(2-chloroethyl)pyridin-3-yl)-4-fluoro-1H-indole

生成物 1

HCID 903336942-Bromo-11-fluoro-5,6-dihydroindolo[2,1-f][1,6]naphthyridine収率 83.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-(5-bromo-2-(2-chloroethyl)pyridin-3-yl)-4-fluoro-1H-indole (800 mg, 2.26 mmol) and cesium carbonate (1.47 g, 4.52 mmol) in 25 mL of DMF was heated at 80° C. for 1 hour. The mixture was concentrated in vacuo to remove DMF, and then the residue was suspended in water and EA. After extraction with EA, the combined organic phase was washed with brine, dried over sodium sulfate and concentrated to afford crude 2-bromo-11-fluoro-5,6-dihydroindolo[2,1-f][1,6]naphthyridine (600 mg, yield: 83.6%) which was used directly in the next step without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.48 (s, 1H), 8.11 (s, 1H), 7.11˜7.17 (m, 2H), 6.97 (s, 1H), 6.78˜6.82 (m, 1H), 4.34˜4.37 (m, 2H), 3.34˜3.37 (m, 2H). MS (M+H)+: 317/319.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove DMF
  3. extractionAfter extraction with EA
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3d2b79bd6ad245169c2c0f4f0c61ba95
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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