Isopropanol → HCID 67085866, compound

HRID 1025276Notes

Reaction equation

HRID 1025276 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[N:6][CH:7]=1.CCN(CC)CC.[CH:25](O)([CH3:27])[CH3:26]>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:25]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[N:6][CH:7]=1)([CH3:27])=[CH2:26]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 10827460HCID 10827460, compound

Product 1

HCID 67085866HCID 67085866, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
80 °C

Procedure

A mixture of benzyl 5-bromopicolinate (2.92 g, 10 mmol), potassium isopropenyl trifluoroborate (3.05 g, 21 mmol), Pd(dppf)Cl2 (445 mg, 0.54 mmol), and Et3N (1.4 mL) in isopropyl alcohol (20 mL) was degassed with N2 and heated at 80° C. for 7 h. The mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with H2O, 5% citric acid, sat. NaHCO3 (aq.) and brine, then dried (MgSO4) and concentrated. The product benzyl 5-isopropenylpicolinate (1.27 g) was obtained by silica gel chromatography (elution with 0-16% EtOAc/Hex).

Workup

  1. customwas degassed with N2
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with H2O, 5% citric acid, sat. NaHCO3 (aq.) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-918fce56c6ee4fac83a100442ef48cfe
Source dataset
uspto-grants-2014_05
Patent number
US08729071B2

Reaction notes

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