Potassium Phosphate, Tribasic → HCID 58547240, compound

HRID 1850277Notes

Reaction equation

HRID 1850277 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:21](Cl)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][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]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:21]([C:28]3[CH:29]=[C:24]([CH3:23])[CH:25]=[CH:26][CH:27]=3)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27339503-Tolylboronic acidHCID 58546996HCID 58546996, compound

Product 1

HCID 58547240HCID 58547240, compoundYield 85%

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 3-(3-chloro-quinoxalin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (46) (639 mg, 2.0 mmol, as prepared in the above Preparation 14), 3-methyl-phenylboronic acid (68) (299.2 mg, 2.2 mmol), K3PO4 (818 mg, 4.0 mmol) in dioxane (20 mL) and water (4 mL) was added Pd(dppf)Cl2 (73.2 mg, 0.1 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 silica gel column to give 3-(3-m-tolyl-quinoxalin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (69) (637 mg, 1.7 mmol, yield 85%).

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 silica gel column

Sources & evidence

ORD record
ord-dc490dc75c984df1ae360345f6b407db
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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