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

HRID 1512838Notes

Reaction equation

HRID 1512838 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-247d7a7e8a1941ce8b8595bbc887034c
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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