Sodium Carbonate → HCID 86590747, compound

HRID 2187647Notes

Reaction equation

HRID 2187647 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](OCCOC)[C:8]([C:12]3[NH:13][CH2:14][CH2:15][N:16]=3)=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.[O:38]1[CH2:43]C[O:41][CH2:40][CH2:39]1>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>[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:12]4[NH:13][CH2:14][CH2:15][N:16]=4)([O:41][CH2:40][CH2:39][O:38][CH3:43])[CH2:9]3)=[CH:4][CH:3]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 79799Tolylboronic acidHCID 10172265HCID 10172265, compound

Product 1

HCID 86590747HCID 86590747, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 1.4 g (4 mmol) of 2-(7-Bromo-3-[2-methoxyethoxy]-naphthalen-2-yl)-4,5-dihydro-1H-imidazole in 80 ml 1,4-dioxane was added under argon 0.46 g (0.4 mmol) of Pd(PPh3)4 and 8 ml of 2M Na2CO3. After stirring at room temperature for 20 minutes 0.816 g 4-methylbenzeneboronic acid was added and the mixture was heated for 20 hours at 80° C. The mixture was cooled to room temperature and filtered to remove the solid. The solution was acidified with 2N HCl and chromatographed on silica gel with dichloromethane/methanole 90/10 and gave 0.52 g (32%) of an amorphus product.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove the solid
  5. customchromatographed on silica gel with dichloromethane/methanole 90/10

Sources & evidence

ORD record
ord-b732fd56870d4b109ec2ebf9aa5d0cb8
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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