Sodium Bicarbonate → 6-[5-(Methylsulfonyl)-3-pyridinyl]-4-(4-pyridinyl)quinoline

HRID 1096773

Reaction equation

HRID 1096773 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[N:26][CH:27]=1)(=[O:21])=[O:20].C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[C:5]3[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:25]=[N:26][CH:27]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 441193815-(Methylsulphonyl)pyridine-3-boronic acidHCID 667822126-Bromo-4-(4-pyridinyl)quinoline

Product 1

HCID 598599746-[5-(Methylsulfonyl)-3-pyridinyl]-4-(4-pyridinyl)quinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (6-bromo-4-(4-pyridinyl)quinoline (250 mg, 0.88 mmol), 5-methylsulfonyl pyridine-3-boronic acid (201 mg, 1.0 mmol), tetrakistriphenylphosphine palladium (0) (104 mg, 0.09 mmol), and sat. aqueous NaHCO3 (1.75 mL), in dioxane (5 mL) was heated at 110° C. for 1 h then cooled to room temperature. The r×n was filtered through Celite and Na2SO4 onto silica and the crude product was purified by column chromatography (5% EtOAc/Hex—10% Ethanol/EtOAc; 30 min gradient). Evaporation and precipitation from MeOH/water (2/98) provided the title compound as a yellow solid. (160 mg, 50%). ESMS [M+H]+=362.1

Workup

  1. filtrationThe r×n was filtered through Celite and Na2SO4 onto silica
  2. customthe crude product was purified by column chromatography (5% EtOAc/Hex—10% Ethanol/EtOAc; 30 min gradient)
  3. customEvaporation and precipitation from MeOH/water (2/98)

Sources & evidence

ORD record
ord-ca7301cdaf3747308f457dadb84a1772
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Linked notes

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