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

HRID 1512830ノート

反応式

HRID 1512830 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 36962535-fluoro-1H-indole-7-carbonitrile収率 64%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-4dee17daa31648788046a520a7107c3a
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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