Potassium Phosphate, Tribasic → tert-Butyl 5-cyclopropylpicolinate

HRID 1842114Notes

Reaction equation

HRID 1842114 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:35]1[CH:36]=[CH:37][C:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:39][CH:40]=1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([C:35]2[CH:36]=[CH:37][C:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:39][CH:40]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

Product 1

HCID 57827284tert-Butyl 5-cyclopropylpicolinateYield 13.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Cyclopropylboronic acid (43.2 mg), tricyclohexylphosphine (10.9 mg), palladium acetate (4.34 mg) and potassium phosphate (288 mg) were added to a mixed solution of tert-butyl 5-bromopyridine-2-carboxylate (100 mg) in toluene (2 mL) and water (100 μL), and the mixture was stirred at 100° C. for nine hours and 30 minutes. After returning to room temperature, water was added to the reaction solution. After extraction with ethyl acetate, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (11.6 mg).

Workup

  1. customAfter returning to room temperature
  2. extractionAfter extraction with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22f91897efa14f46b71e2cc63df947c2
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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