Potassium Carbonate → HCID 53217788, compound

HRID 930758Notes

Reaction equation

HRID 930758 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[CH:3]=1.[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.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.Cl[Pd]Cl.[Fe+2]>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 140623094-Bromo-2-methoxypyridine

Product 1

HCID 53217788HCID 53217788, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 4-bromo-2-methoxypyridine (1.225 g, 6.511 mmol), 4-methylthiophenyl boronic acid (2.188 g, 13.02 mmol), PdCl2(dppf) (531 mg, 0.651 mmol) and K2CO3 (1.797 g, 13.02 mmol) in DMSO (10 mL) was degassed under reduced pressure for 25 min. The suspension was put under N2 and stirred at 95° C. for 16 h. The suspension was cooled, H2O was added, and the suspension was filtered to afford a light colored solid. Flash chromatography (silica gel, hexanes/(1:1 EtOAc/hexanes), 100:0 to 0:100) afforded 1.10 g of a white powder. The white powder was diluted with concentrated HCl solution (50 mL) and stirred at reflux for 24 h. The reaction was cooled and concentrated under reduced pressure. The residue was neutralized with saturated NaHCO3 solution, and the solid was collected by filtration. The solid was washed with H2O to afford the title compound (1.103 g, 71%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 7.65 (d, J=8.4 Hz, 2H), 7.43 (d, J=6.9 Hz, 1H), 7.34 (d, J=8.4 Hz, 2H), 6.57 (d, J=1.7 Hz, 1H), 6.50 (dd, J=6.9, 1.7 Hz, 1H), 3.34 (s, 3H).

Workup

  1. customwas degassed under reduced pressure for 25 min
  2. temperatureThe suspension was cooled
  3. additionH2O was added
  4. filtrationthe suspension was filtered
  5. customto afford a light colored solid

Sources & evidence

ORD record
ord-1c505dace87e4ba698d867737df62f35
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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