Dimethylformamide → 6-fluoro-1H-indole-7-carbonitrile

HRID 1512838노트

반응식

HRID 1512838 반응식
Br[C:2]1[C:3]([F:11])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[F:11][C:3]1[C:2]([C:12]#[N:13])=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 269860207-Bromo-6-fluoro-1H-indole

생성물 1

HCID 591461546-fluoro-1H-indole-7-carbonitrile

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

실험 절차

To a solution of 7-bromo-6-fluoro-1H-indole (D140) (1.0 g) in DMF (15 ml) were added Zn(CN)2 (2.2 g) and then Pd(PPh3)4 (1.1 g) in a microwave tube, then N2 atmosphere was bubbled in. The sealed vial was irradiated in the microwave at 150° C. for 2 hours. After cooling, DCM (80 mL) was added to the resulting mixture which was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to afford 6-fluoro-1H-indole-7-carbonitrile (D141) (0.5 g) as a white solid.

후처리

  1. customPd(PPh3)4 (1.1 g) in a microwave tube, then N2 atmosphere was bubbled in
  2. customThe sealed vial was irradiated in the microwave at 150° C. for 2 hours
  3. temperatureAfter cooling
  4. additionDCM (80 mL) was added to the resulting mixture which
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-247d7a7e8a1941ce8b8595bbc887034c
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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