Sodium Carbonate → HCID 178489509, compound

HRID 929672Notes

Reaction equation

C(O)(=O)C.Br[C:6]1[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[NH:14])=[N:8][CH:9]=[CH:10][CH:11]=1.[C:25]1(OB(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][NH:15][C:13]([NH:12][C:7]1[C:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)=[NH:14]

Participants

Reactant 3

HCID 10340Sodium Carbonate

HCID 78412Phenyl dihydrogen orthoborate

HCID 178476649HCID 178476649, compound

Product 1

HCID 178489509HCID 178489509, compoundYield 19%

Conditions

Temperature: 110 °C

Procedure

The preparation was carried out analogously to Example 56, using 0.200 g (0.506 mmol) N-(3-bromopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine acetate, 0.092 g (0.759 mmol) phenylboric acid, 0.165 g (1.518 mmol) sodium carbonate, and 0.040 g (0.035 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block at 110° C., first for 21 hr and then for an additional 20 hr, for a total of 41 hr under a nitrogen atmosphere. After appropriate workup and purification via preparative HPLC, 32 mg pure N-(2-methoxybenzyl)-N′-(3-phenylpyridin-2-yl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1.2).

Workup

customfor a total of 41 hr
customAfter appropriate workup and purification via preparative HPLC

Sources & evidence

ORD record: ord-3769e27522f24929b72238a73220deb6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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