Potassium Phosphate, Tribasic → HCID 54671179, compound

HRID 1842528Notes

Reaction equation

HRID 1842528 reaction equation
Br[C:2]1[C:3]([N:8]2[CH2:11][CH: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.[O:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)[CH3:23].[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]>[CH3:23][O:22][C:24]1[CH:29]=[C:28]([C:2]2[C:3]([N:8]3[CH2:11][CH: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 58548420HCID 58548420, compound

Product 1

HCID 54671179HCID 54671179, compoundYield 35%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
110 °C

Procedure

To a solution of 2-[1-(3-bromo-pyridin-2-yl)-azetidin-3-yl]-quinoline, as prepared in the above Step 1 of Example 59, (150 mg, 0.44 mmol), 3-methoxyl-phenylboronic acid (80 mg, 0.51 mmol) and K3PO4 (211 mg, 1 mmol) in 1,4-dioxane (12 mL) and H2O (3 mL) was added Pd(dppf)Cl2 (35 mg, 0.05 mmol) then the reaction mixture was stirred at 110° C. under N2 overnight. The reaction mixture was filtered through CELITE™ and washed with CH2Cl2 (50 mL). The organic layer was concentrated and the crude product was purified by silica gel column to give 2-{1-[3-(3-methoxy-phenyl)-pyridin-2-yl]-azetidin-3-yl}-quinoline (70 mg, 0.19 mmol, yield 35%).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE™
  2. washwashed with CH2Cl2 (50 mL)
  3. concentrationThe organic layer was concentrated
  4. customthe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-d9ce07e2d0bc4d6dbaea0a61ce08ef6d
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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