(2-Methoxypyridin-3-yl)boronic acid → HCID 86614001, compound

HRID 643001Notes

Reaction equation

HRID 643001 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][C:14]3[CH:18]=[CH:17][S:16][C:15]=3[C:19]([NH2:21])=[O:20])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][O:23][C:24]1[C:29]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:12]=[C:11]([CH2:13][C:14]4[CH:18]=[CH:17][S:16][C:15]=4[C:19]([NH2:21])=[O:20])[N:10]=[CH:9]3)=[CH:4][CH:3]=2)=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 86614002HCID 86614002, compound

Product 1

HCID 86614001HCID 86614001, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-N-((1-(4-iodophenyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (0.044 g, 0.1 mmol), 2-methoxypyridine-3-ylboronic acid (0.016 g, 0.11 mmol) and Pd(PPh3)2Cl2 (0.007 g, 0.01 mmol) in p-dioxane (0.7 mL) was purged with Argon for 5 min. A degassed aqueous solution of Na2CO3 (IM, 0.3 mL) was added. After being heated at 100° C. for 2 h, the mixture was cooled to room temperature, and purified by preparative HPLC to yield 5-chloro-N-((1-(4-(2-methoxypyridin-3-yl)phenyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (MS 425.0, 427.0 (M+H), Cl pattern).

Workup

  1. customwas purged with Argon for 5 min
  2. additionA degassed aqueous solution of Na2CO3 (IM, 0.3 mL) was added
  3. temperaturethe mixture was cooled to room temperature
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-26b86d36fc3447ed84e79ec30215abfa
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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