Sodium Carbonate → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide
Reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8](Br)[CH:7]=1)=[O:5])[CH3:2].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O.C(O)C>[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)(=O)C>[CH2:1]([NH:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
7-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide (0.160 g, 0.450 mmol), pyridine-3-boronic acid (0.0910 g, 0.742 mmol), sodium carbonate (0.215 g, 2.03 mmol), and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.005 g) were suspended in a solution of ethylene glycol dimethyl ether/water/ethanol (7:3:2, 6.00 mL) and subjected to microwave at 80° C. for 30 minutes. The reaction mixture was acidified with acetic acid and purified by column chromatography (gradient 0-5% methanol/dichloromethane) to afford the desired product 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide MS (APCI+): m/z 354.3 (M+H).
Workup
- custompurified by column chromatography (gradient 0-5% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-0672266da5224b098e67095865d4d97c
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524860B2
Reaction notes
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