Potassium Carbonate → (3-Bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl ester

HRID 1784886Notes

Reaction equation

HRID 1784886 reaction equation
[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:10]=[C:9](I)[CH:8]=[C:7]([Br:12])[CH:6]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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]>[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:10]=[C:9]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[CH:8]=[C:7]([Br:12])[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 68843615(3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester

Product 1

HCID 68843413(3-Bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl esterYield 38.3%

Reagents, catalysts & solvents 2

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

Procedure

(3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester (0.22 g, 0.62 mmol), 3-pyridylboronic acid (0.11 g, 0.93 mmol), and Pd(dppf)Cl2.CH2Cl2 complex (0.051 g, 0.062 mmol) were dissolved in dioxane (6 mL). Aqueous 2 M potassium carbonate (0.26 g, 1.9 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was then heated to 60° C. for 24 hrs. The reaction mixture was filtered through Celite® and the solvent was removed. The product was chromatographed to give 0.073 g (38% yield) of (3-bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl ester.

Workup

  1. temperatureThe reaction mixture was then heated to 60° C. for 24 hrs
  2. filtrationThe reaction mixture was filtered through Celite®
  3. customthe solvent was removed
  4. customThe product was chromatographed

Sources & evidence

ORD record
ord-0d665081fa7442c3a4216bae27b5bc2c
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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