Sodium Carbonate → HCID 178489503, compound

HRID 929680Notes

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.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1OB(O)O.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>[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:22]2[S:21][CH:25]=[CH:24][CH:23]=2)=[CH:7][N:6]=1)=[NH:10]

Participants

Conditions

Temperature: 120 °C

Procedure

The preparation was carried out analogously to Example 86, using 0.125 g (0.308 mmol) N-(5-iodopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine, 0.055 g (0.431 mmol) 2-thienylboric acid, 0.098 g (0.925 mmol) sodium carbonate, and 0.018 g (0.015 mmol) tetrakis-(triphenylphosphine)-palladium(0). The mixture was likewise heated for 60 min at 120° C. in a CEM microwave (200 watts). After filtration and purification via preparative HPLC, 23 mg N-(2-methoxybenzyl)-N′-[5-(2-thienyl)pyridin-2-yl]guanidine was isolated, a small portion of which was present in the form of the acetate salt (base/acetate in a ratio of 1:0.3).

Workup

filtrationAfter filtration and purification via preparative HPLC

Sources & evidence

ORD record: ord-4c33ddf05dc042cdb9fb778bd7f0aac5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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