Nitrogen → HCID 58276770, compound

HRID 70333Notes

Reaction equation

HRID 70333 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)=[N:8]1)=[O:4].[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].C(Cl)Cl.N#N.C([O-])([O-])=O.[Na+].[Na+]>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].C1(C)C=CC=CC=1.CCO>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[C:14]([C:26]3[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=3)[CH:15]=[CH:16][CH:17]=2)=[N:8]1)=[O:4]

Participants

8

Reactant 5

HCID 947NitrogenHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 58276234[3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate

Product 1

HCID 58276770HCID 58276770, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A vial equipped with magnetic spin vane was charged with [[3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.203 g; 0.60 mmol; Ex IV-24), 4-formylphenyl boronic acid (0.099 g; 0.66 mmol), and PdCl2(dppf).CH2Cl2 (0.012 g; 0.015 mmol), was sealed with a septum and evacuated/backfilled with N2 (×3). PhMe/EtOH (4:1, 3 mL) and 2M Na2CO3 (0.72 mL; 1.44 mmol) were added through the septum via syringe and the mixture was stirred at 80° C. for 2.5 h. Upon cooling, the mixture was partitioned between EtOAc/water and the layers were separated. The aqueous layer was extracted with EtOAc (×2), combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum/film. LC/MS (method A) 2.60 min; m/z 364 (M+H).

Workup

  1. customA vial equipped with magnetic spin vane
  2. temperatureUpon cooling
  3. customthe mixture was partitioned between EtOAc/water
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (×2)
  6. washcombined organics were washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f0c34c04c3246e0b91efc9283b60910
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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