N-methyl-2-pyrrolidone → HCID 178509430, compound

HRID 475154Notes

Reaction equation

HRID 475154 reaction equation
Br[C:2]1[C:3]([F:11])=[CH:4][C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.[CH3:12][N:13]1C(=O)CCC1>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.[C-]#N.[C-]#N.[Zn+2]>[F:11][C:3]1[C:2]([C:12]#[N:13])=[CH:10][C:6]2[NH:7][CH:8]=[N:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 178505400HCID 178505400, compound

Product 1

HCID 178509430HCID 178509430, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-5-fluoro-1H-benzo[d]imidazole (10.0 g, 46.5 mmol), Pd(PPh3)4 (7.97 g, 6.9 mmol), and Zn(CN)2 (8.46 g, 93 mmol) in NMP (150 mL) under nitrogen was heated at 110° C. for 16 h. The reaction mixture was quenched with water and extracted with EtOAc (100 mL×5). The combined extracts were washed with brine (300 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford 6-fluoro-3H-benzo[d]imidazole-5-carbonitrile as white solid (7.0 g, 93.5%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (100 mL×5)
  3. washThe combined extracts were washed with brine (300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03866fa874fb4195a05112e3f312c82b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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