Potassium Carbonate → HCID 58044326, compound

HRID 2368025Notes

Reaction equation

HRID 2368025 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH2:9][N:10]2[C:29](=[O:30])[N:13]3[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[CH:16]=[CH:17][C:12]3=[N:11]2)[CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:31]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH2:9][N:10]3[C:29](=[O:30])[N:13]4[CH:14]=[C:15]([C:18]5[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=5)[CH:16]=[CH:17][C:12]4=[N:11]3)[CH:3]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 58044313HCID 58044313, compound

Product 1

HCID 58044326HCID 58044326, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(2-(4-bromopyridin-2-yl)ethyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (synthesized according to Example 1, 40 mg, 0.084 mmol), cyclopropyl boronic acid (22 mg, 0.25 mmol), dppf(Pd)Cl2 (9.0 mg, 0.013 mmol), potassium carbonate (46 mg, 0.33 mmol) in degassed dioxane (1 mL) was heated at 100° C. for 3 hours. The reaction was concentrated and the residue was purified by reverse phase HPLC to provide compound 57 as a white powder (30 mg, 81% yield). C23H19F3N4O2, m/z (ESI)=441.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c4e97c4a017d4195837c1cd6e0df1603
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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