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

HRID 595682노트

반응식

HRID 595682 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d2b79bd6ad245169c2c0f4f0c61ba95
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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