Sodium Carbonate → HCID 178489499, compound

HRID 929668Notes

Reaction equation

HRID 929668 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([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])[CH:3]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[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:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[CH:6][N:5]=1)=[NH:10]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 178489498HCID 178489498, compound

Product 1

HCID 178489499HCID 178489499, compoundYield 35%

Conditions

Temperature
110 °C

Procedure

The preparation was carried out analogously to Example 56, using 0.150 g (0.447 mmol) N-(4-bromopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine, 0.081 g (0.651 mmol) phenylboric acid, 0.142 g (1.343 mmol) sodium carbonate, and 0.036 g (0.031 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 17.5 hr at 110° C. under a nitrogen atmosphere. After appropriate workup and purification via preparative HPLC, 52 mg pure N-(2-methoxybenzyl)-N′-(4-phenylpyridin-2-yl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1.2).

Workup

  1. customAfter appropriate workup and purification via preparative HPLC

Sources & evidence

ORD record
ord-564b75cc849e41508505458e860bb7c5
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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