Acetate → HCID 178489500, compound

HRID 929669Notes

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

Participants

Reactant 4

HCID 175Acetate

HCID 10340Sodium Carbonate

HCID 219397714-Fluoro-phenylboric acid

HCID 178489498HCID 178489498, compound

Product 1

HCID 178489500HCID 178489500, compoundYield 27.7%

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, 0.093 g (0.671 mmol) (4-fluorophenyl)boric 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, 50.9 mg (0.124 mmol, 27%) pure N-[4-(4-fluorophenyl)pyridin-2-yl]-N′-(2-methoxybenzyl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1).

Workup

customAfter appropriate workup and purification via preparative HPLC

Sources & evidence

ORD record: ord-f20779d7723f40e69fb460839795fbd8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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