Sodium Cyanide → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

HRID 1037560노트

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HRID 1037560 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2Cl.[C-:19]#[N:20].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:19]#[N:20]

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 677760136-bromo-3-chloro-2-(4-fluorophenyl)-2H-indazole

생성물 1

HCID 675136096-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile수율 54.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

To a stirred solution of compound (xiii) (4.49 g, 12.86 mmol) in DMF (50 mL) was added sodium cyanide (1.34 g, 27.73 mmol) at RT and the reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then diluted with saturated FeCl3 solution and extracted with EtOAc (3×75 mL). The combined organic layers were washed with water, dried (Na2SO4) and concentrated to give the crude product which was purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%) to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (xiv) (2.2 g, 50%) as white solid. ESI-MS m/z calculated for [M+H]+: 317.99; found: 317.90.

후처리

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%)

출처 및 근거

ORD 기록
ord-523d92fec85e47b1901a491436473d00
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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