Sodium Carbonate → HCID 178491349, compound

HRID 929666Notes

Reaction equation

HRID 929666 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11][CH2:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH3:22])=[NH:10])[CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](OB(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(O)C>[CH3:22][O:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1[CH2:12][NH:11][C:9]([NH:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[N:7]=1)=[NH:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 219397714-Fluoro-phenylboric acidHCID 178491347HCID 178491347, compound

Product 1

HCID 178491349HCID 178491349, compound

Reagents, catalysts & solvents 1

HCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

0.254 g (0.695 mmol) N-(6-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine, 0.128 g (0.913 mmol) 4-fluorophenylboric acid, 0.239 g (2.258 mmol) sodium carbonate, and 0.055 g (0.047 mmol) tetrakis-(triphenylphosphine)palladium(0) were heated to 110° C. in 1,2-dimethoxyethane/water/ethanol (7:3:2) in a reaction block (Variomag, Telemodul 40 CT) at standard pressure. Upon cooling of the reaction mixture a yellow solid precipitated, which was suctioned off and washed with water. After the yellow solid was dissolved in methanol and dichloromethane the catalyst was separated via a Millipore filter (Ø=25 mm, 0.45 μm). The target product N-(2,6-dimethoxybenzyl)-N′-[6-(4-fluorophenyl)pyridin-2-yl]guanidine was in the pure form after the removal of solvent, and the yield was 0.214 g (0.563 mmol, 81%).

Workup

  1. temperatureUpon cooling of the reaction mixture a yellow solid
  2. customprecipitated
  3. washwashed with water
  4. dissolutionAfter the yellow solid was dissolved in methanol
  5. customdichloromethane the catalyst was separated via a Millipore
  6. filtrationfilter (Ø=25 mm, 0.45 μm)
  7. customafter the removal of solvent

Sources & evidence

ORD record
ord-41997d4e193c43b5acb0aa3bfef72fdd
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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