Water → HCID 59589925, compound

HRID 1049666Notes

Reaction equation

HRID 1049666 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[N:18]2[N:19]=[C:20]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[N:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.O.Cl[Pd]Cl.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.[Fe+2]>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[N:18]3[N:19]=[C:20]([NH:22][C:23]([CH:25]4[CH2:26][CH2:27]4)=[O:24])[N:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 59179473N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 59589925HCID 59589925, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

4-(Hydroxymethyl)phenylboronic acid (1.1 eq.) is added to a solution of cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide in 1,4-dioxane/water (4:1). K2CO3 (2 eq.) and PdCl2 dppf (0.03 eq.) are added to the solution. The resulting mixture is then heated in an oil bath at 90° C. for 16 h under N2. Water is added and the solution is extracted with ethyl acetate. The organic layers are dried over anhydrous MgSO4 and evaporated in vacuo. The resulting mixture is used without further purification.

Workup

  1. extractionthe solution is extracted with ethyl acetate
  2. dry with materialThe organic layers are dried over anhydrous MgSO4
  3. customevaporated in vacuo
  4. customThe resulting mixture is used without further purification

Sources & evidence

ORD record
ord-13a6cfa685694643b2a8a5785fa1c046
Source dataset
uspto-grants-2016_07
Patent number
US09382247B2

Reaction notes

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