Potassium Phosphate, Tribasic → HCID 58547005, compound

HRID 1850343Notes

Reaction equation

HRID 1850343 reaction equation
Br[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[CH3:22][O:23][C:24]1[CH:29]=[C:28]([C:2]2[C:3]([CH:8]3[CH2:11][N:10]([C:12]4[CH:21]=[CH:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH2:9]3)=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 58547111HCID 58547111, compound

Product 1

HCID 58547005HCID 58547005, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-[3-(3-bromo-pyridin-2-yl)-azetidin-1-yl]-quinoline (339 mg, 1 mmol), 3-methoxy-phenylboronic acid (167.2 mg, 1.1 mmol), K3PO4 (414 mg, 2.0 mmol) in dioxane (20 mL) and water (2 mL) was added Pd(dppf)Cl2 (36.6 mg, 0.05 mmol) then the reaction mixture was stirred at 90° C. under nitrogen atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether) to give 2-{3-[3-(3-methoxy-phenyl)-pyridin-2-yl]-azetidin-1-yl}-quinoline (132 mg, 0.36 mmol, yield 36%).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washwashed with EtOAc (50 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by ISCO silica gel column (10% to 80% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-e62810dfbf204dfca0247588b54d567c
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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