HCID 66782145, compound → HCID 178419956, compound

HRID 1952294Notes

Reaction equation

HRID 1952294 reaction equation
Br[C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[N:8][C:5]2=[N:6][CH:7]=1.[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([Sn](C)(C)C)[CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>O1CCOCC1>[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:2]4[CH:3]=[C:4]5[NH:10][N:9]=[N:8][C:5]5=[N:6][CH:7]=4)[CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 66782145HCID 66782145, compoundHCID 178419454HCID 178419454, compound

Product 1

HCID 178419956HCID 178419956, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-1H-[1,2,3]triazolo[4,5-b]pyridine (100 mg, 0.5 mmol), 4-(4-pyridinyl)-6-(trimethylstannanyl)quinoline (204 mg, 0.55 mmol), and tetrakistriphenylphosphine palladium(0) (29 mg, 0.025 mmol) in 1,4-dioxane (3.0 mL) was heated at 100° C. for 18 h. The reaction was filtered to collect the precipitate. The solid was triturated in hot ethanol to give an off-white solid, which still contained some minor impurities. The off-white solid was triturated in hot ethanol to give the title product as a beige solid (22 mg, 14%). MS(ES)+ m/e 325.1 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. customto collect the precipitate
  3. customThe solid was triturated in hot ethanol
  4. customto give an off-white solid, which
  5. customThe off-white solid was triturated in hot ethanol

Sources & evidence

ORD record
ord-6821355b2bec41e4ba8c3ba7b7cf45b4
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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