Dimethylformamide → HCID 25194664, compound

HRID 2366458Notes

Reaction equation

HRID 2366458 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:12].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:12][C:3]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[C:13]#[N:14]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 2920042-Bromo-4-fluoro-6-nitroaniline

Product 1

HCID 25194664HCID 25194664, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A suspension of EXAMPLE 45A (22.7 g), zinc cyanide (22.6 g) and tetrakis(triphenylphosphine) palladium (7.78 g) in anhydrous DMF (300 mL) was heated at 80° C. for 22 hours. After cooling, the reaction mixture was partitioned between ethyl acetate (500 mL) and brine (500 mL). The organic phase was washed with water and concentrated. Recrystallization of the concentrate from methanol provided EXAMPLE 45B.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate (500 mL) and brine (500 mL)
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customRecrystallization of the
  6. concentrationconcentrate from methanol
  7. customprovided EXAMPLE 45B

Sources & evidence

ORD record
ord-cc1e0c0125ae4b14ae34043e1b14bd7d
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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