Potassium Carbonate → HCID 86698652, compound

HRID 338305Notes

Reaction equation

HRID 338305 reaction equation
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CCO.C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([CH3:10])[CH:9]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57736551HCID 57736551, compound

Product 1

HCID 86698652HCID 86698652, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-4-methyl-5-nitro-benzonitrile (522.0 mg, 2.17 mmol), 4-methoxyphenyl boronic acid (329.0 mg, 2.17 mmol) and 2N aqueous potassium carbonate (6.56 mL, 13.1 mmol) in EtOH (6 mL) and toluene (3 mL) was degassed with N2 for 5 minutes, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (180.0 mg, 0.22 mmol), and degassed with N2 for an additional 5 minutes. The reaction mixture was sealed and heated to 80° C. for 3 hours. The reaction was cooled to room temperature and the layers were separated. The organic layer was filtered and the solids were air dried to give the title compound (145 mg). The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (25-75% EtOAc/heptane) to give the title compound (337 mg). The two lots of the title compound were combined (482 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.78 (s, 1H), 7.63 (d, J=8.78 Hz, 2H), 7.14 (d, J=8.59 Hz, 2H), 3.85 (s, 3H), 2.64 (s, 3H).

Workup

  1. customwas degassed with N2 for 5 minutes
  2. customdegassed with N2 for an additional 5 minutes
  3. customThe reaction mixture was sealed
  4. temperatureThe reaction was cooled to room temperature
  5. customthe layers were separated
  6. filtrationThe organic layer was filtered
  7. customdried

Sources & evidence

ORD record
ord-6fdfd8a305864dfdaf435e34d2f45bd7
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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