Potassium Phosphate, Tribasic → Ethyl 6-cyclopropylpicolinate

HRID 334044Notes

Reaction equation

HRID 334044 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[N:7]=1)=[O:5])[CH3:2].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:13]2[CH2:15][CH2:14]2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, Tribasic2×HCID 2758810Ethyl 6-BromopicolinateHCID 2760897Cyclopropylboronic acid2×

Product 1

HCID 86688276Ethyl 6-cyclopropylpicolinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2.90 g (12.6 mmol) 6-bromo-pyridine-2-carboxylic acid ethyl ester in 25 mL toluene was added 3.00 g (29.7 mmol) cyclopropylboronic acid and 5.50 g (25.9 mmol) potassium phosphate followed by 700 mg (0.957 mmol) 1,1′-bis(diphenylphosphino)-ferrocenedichloropalladium(II). The reaction mixture was stirred at 100° C. for 8 h. 1.00 g (9.90 mmol) of cyclopropylboronic acid and 1.50 g (7.07 mmol) of potassium phosphate were added and the mixture was stirred at 100° C. for 5 h. The reaction mixture was filtered through Celite, and washed with DCM and the solvent was evaporated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=4/1→2/1).

Workup

  1. stirringthe mixture was stirred at 100° C. for 5 h
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashed with DCM
  4. customthe solvent was evaporated in vacuo
  5. customThe crude material was purified by flash chromatography (PE/EtOAc=4/1→2/1)

Sources & evidence

ORD record
ord-ce36797fad314a8898e5b73e5009c336
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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