Sodium Carbonate → 4'-Amino-2'-fluoro-5'-nitrobiphenyl-4-carbonitrile

HRID 1424229Notes

Reaction equation

HRID 1424229 reaction equation
Br[C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.[Pd+2].ClC1C=C[C-](P(C(C)(C)C)C(C)(C)C)C=1Cl.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[NH2:6][C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]([C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[C:8]([F:9])[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 219119284-Bromo-5-fluoro-2-nitroaniline

Product 1

HCID 866991314'-Amino-2'-fluoro-5'-nitrobiphenyl-4-carbonitrileYield 93.1%

Reagents, catalysts & solvents 2

HCID 178454866HCID 178454866, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4-bromo-5-fluoro-2-nitroaniline (0.8 g, 3.8 mmol), 4-cyanophenylboronic acid (0.58 g, 3.87 mmol) and sodium carbonate (1 g, 9.50 mmol) in THF/water (15 mL/2 mL) was degassed with nitrogen for 10 minutes. To the suspension was added dichloro [1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (80 mg, 0.095 mmol) and the reaction was heated to 60° C. for 18 hours. The reaction was filtered through celite and the filtrate diluted with water and EtOAc. The organic layer was collected and concentrated in vacuo to afford the title compound as a yellow solid (0.91 g, 91%).

Workup

  1. customwas degassed with nitrogen for 10 minutes
  2. filtrationThe reaction was filtered through celite
  3. additionthe filtrate diluted with water and EtOAc
  4. customThe organic layer was collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6bab6169b03b4514bb2be06770e1acf8
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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