3-Pyridinylboronic acid → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

HRID 2112957Notes

Reaction equation

HRID 2112957 reaction equation
[CH2:1]([O: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.O.O.O.C([O-])(=O)C.[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC.O.CCO>[CH2:1]([O: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

6

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 23665404Sodium Acetate TrihydrateHCID 576430687-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 576431092-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of the product of Step 1 (0.145 g, 0.407 mmol), 3-pyridylboronic acid (0.092 g, 0.750 mmol), sodium acetate trihydrate (0.308 g, 2.08 mmol), and 0.013 g Pd(dppf)Cl2-DCM in a mixture of 7:3:2 DME/water/EtOH (6 mL) was heated to 80° C. for 30 min in a closed vial in a CEM microwave reactor. The reaction was then partitioned between saturated sodium bicarbonate and DCM and the organic layer was collected. The aqueous layer was extracted with DCM (2×25 mL) and the combined organic layers were then extracted with 1N HCl (3×10 mL). The combined aqueous extracts were then neutralized with solid sodium bicarbonate and extracted with DCM (3×20 mL). The combined organic layers were then dried over sodium sulfate and evaporated in vacuo to give 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester as a powder. MS (APCI+)=355.2

Workup

  1. customThe reaction was then partitioned between saturated sodium bicarbonate and DCM
  2. customthe organic layer was collected
  3. extractionThe aqueous layer was extracted with DCM (2×25 mL)
  4. extractionthe combined organic layers were then extracted with 1N HCl (3×10 mL)
  5. extractionextracted with DCM (3×20 mL)
  6. dry with materialThe combined organic layers were then dried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2837d9ad9f2544f6aba904004365a523
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

Loading…