Acetate → HCID 178489510, compound
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.[F:25][C:26]1[CH:31]=[CH:30][C:29](OB(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:6]2[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[NH:14])=[N:8][CH:9]=[CH:10][CH:11]=2)=[CH:28][CH:27]=1Participants
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, 0.106 g (0.759 mmol) (4-fluorophenyl)boric acid, 0.160 g (1.518 mmol) sodium carbonate, and 0.038 g (0.033 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 19 hr at 110° C. under a nitrogen atmosphere. Despite prolonging the reaction time to a total of 6 days and renewed addition of the starting materials sodium carbonate, (4-fluorophenyl)boric acid, and catalyst, the reaction reached an end point at which the starting material/product-ratio of 1:1 had not changed. After termination of the reaction, appropriate workup, and purification via preparative HPLC, 20 mg (0.048 mmol, 9.4%) pure N-[3-(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
- customto a total of 6 days
- customAfter termination of the reaction, appropriate workup, and purification via preparative HPLC
Sources & evidence
- ORD record
- ord-e339ce79494c4d5db236dd35c6a10d0f
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296697B2
Reaction notes
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