HCID 10827460, compound → HCID 67085659, compound

HRID 1429685Notes

Reaction equation

HRID 1429685 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.[Br-].[CH:19]1([Zn+])[CH2:21][CH2:20]1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])=[N:6][CH:7]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 10827460HCID 10827460, compoundHCID 178419765HCID 178419765, compound

Product 1

HCID 67085659HCID 67085659, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl 5-bromopicolinate (876 mg, 3.0 mmol) in THF (10 mL) was added Pd(PPh3)4 (173 mg, 0.15 mmol) under N2. After addition of a solution of cyclopropylzinc bromide in THF (0.5 M, 10 mL), the mixture was heated at 80° C. for 3 hours and then cooled to room temperature. The reaction mixture was quenched with sat. NH4Cl (aq) and extracted with EtOAc (3×). The organic layer was washed with sat. NaHCO3(aq.), brine, and dried (MgSO4). The product benzyl 5-cyclopropylpicolinate (510 mg) was obtained by silica gel chromatography (elution with 0-15% EtOAc/Hex, then 15% EtOAc/Hex).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was quenched with sat. NH4Cl (aq)
  3. extractionextracted with EtOAc (3×)
  4. washThe organic layer was washed with sat. NaHCO3(aq.), brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-48e3b7aa439e4492b9edd913e049e347
Source dataset
uspto-grants-2015_01
Patent number
US08940748B2

Reaction notes

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