Toluene → HCID 15949563, compound

HRID 646269Notes

Reaction equation

HRID 646269 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[N:10]([CH3:31])[C:11](=[O:30])[C:12]([C:21]2[CH:22]=[C:23]([CH:28]=[O:29])[N:24]([CH2:26][CH3:27])[CH:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=2)[N:13]=1.[F:32][C:33]1[C:38](B(O)O)=[CH:37][CH:36]=[CH:35][N:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C(O)C>[NH2:8][C:9]1[N:10]([CH3:31])[C:11](=[O:30])[C:12]([C:21]2[CH:22]=[C:23]([CH:28]=[O:29])[N:24]([CH2:26][CH3:27])[CH:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:38]3[C:33]([F:32])=[N:34][CH:35]=[CH:36][CH:37]=3)[CH:15]=2)[N:13]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 15949655HCID 15949655, compound

Product 1

HCID 15949563HCID 15949563, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A 1:1 mixture of toluene and ethanol was sparged with nitrogen for 30 minutes. To the solvent was added 4-[2-amino-4-(3-bromophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1-ethyl-1H-pyrrole-2-carbaldehyde (1.10 g; 3.04 mmol), 2-fluoro-3-pyridineboronic acid (0.69 g; 4.9 mmol), sodium carbonate (1.03 g; 9.75 mmol), and tetrakis[triphenylphosphine]-palladium(0) (0.53 g; 0.46 mmol). This mixture was heated at reflux temperature for three hours. The solvents were evaporated and the residue was crystallized in CHCl3 and water to give the title as grey crystals, 0.91 g (74% yield),

Workup

  1. customwas sparged with nitrogen for 30 minutes
  2. temperatureThis mixture was heated
  3. temperatureat reflux temperature for three hours
  4. customThe solvents were evaporated
  5. customthe residue was crystallized in CHCl3
  6. customwater to give the title as grey crystals, 0.91 g (74% yield)

Sources & evidence

ORD record
ord-995e2f94a8f6487aaeebf3cd689fa18a
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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