Sodium Carbonate → HCID 178489501, compound

HRID 929679Notes

Reaction equation

HRID 929679 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[NH:10])=[N:6][CH:7]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC.O.C(O)C>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][NH:11][C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][N:6]=1)=[NH:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 178489507HCID 178489507, compound

Product 1

HCID 178489501HCID 178489501, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
120 °C

Procedure

0.102 g (0.251 mmol) N-(5-iodopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine, 0.041 g (0.337 mmol) phenylboric acid, 0.075 g (0.708 mmol) sodium carbonate, and 0.015 g (0.013 mmol) tetrakis-(triphenylphosphine) palladium(0) were combined and added to 7.0 mL of a solvent mixture of 1,2-dimethoxyethane/water/ethanol (7:3:2). The mixture was degassed under a strong nitrogen stream and heated for 110 min at 120° C. in a CEM microwave (150 watts) and reacted. After filtration through a Millipore filter (Ø=25 mm, 0.45 μm) the solvent was removed under vacuum and the crude mixture was purified via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid), with a flow rate of 20 mL/min and with gradients of 10% to 30% of the acetonitrile fraction in 10 min. Following freeze drying with a lyophilizing agent, 23 mg of the desired product N-(2-methoxybenzyl)-N′-(5-phenylpyridin-2-yl)guanidine was isolated.

Workup

  1. customThe mixture was degassed under a strong nitrogen stream
  2. customreacted
  3. filtrationAfter filtration through a Millipore
  4. filtrationfilter (Ø=25 mm, 0.45 μm) the solvent
  5. customwas removed under vacuum
  6. customthe crude mixture was purified via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid), with a flow rate of 20 mL/min and with gradients of 10% to 30% of the acetonitrile fraction in 10 min
  7. customdrying with a lyophilizing agent

Sources & evidence

ORD record
ord-06404a8f9d554805a7124517806a6b4f
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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