Dimethylformamide → 5-fluoro-1H-indole-7-carbonitrile

HRID 1512830노트

반응식

HRID 1512830 반응식
Br[C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(Cl)Cl.[CH3:15][N:16](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:15]#[N:16])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 38528797-bromo-5-fluoro-1H-indole

생성물 1

HCID 36962535-fluoro-1H-indole-7-carbonitrile수율 64%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To a solution of 7-bromo-5-fluoro-1H-indole (D131) (15 g) in DMF (150 mL) under N2 atmosphere were added Zn(CN)2 (24.0 g) and then Pd(PPh3)4 (15.8 g), the reaction mixture was heated to 120° C. and stirred overnight. After cooling, DCM (300 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 7 g (64% yield) of 5-fluoro-1H-indole-7-carbonitrile (D132) as a white solid. δH (CDCl3, 400 MHz): 6.51 (1H, t), 7.20 (1H, dd), 7.30 (1H, t), 7.52 (1H, dd), 8.82 (1H, br s).

후처리

  1. temperatureAfter cooling
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-4dee17daa31648788046a520a7107c3a
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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