ChemicalBook CAS DataBase List Methyl 5-bromo-6-chloropyridine-3-carboxylate

Methyl 5-bromo-6-chloropyridine-3-carboxylate synthesis

15synthesis methods

Product Name:Methyl 5-bromo-6-chloropyridine-3-carboxylate
CAS Number:78686-77-8
Molecular formula:C7H5BrClNO2
Molecular Weight:250.48

29241-62-1

74-88-4

Methyl 5-bromo-6-chloropyridine-3-carboxylate

78686-77-8

Step 1: Synthesis of methyl 5-bromo-6-chloronicotinate (61). A mixture of 5-bromo-6-chloronicotinic acid (60) (0.2 g, 0.84 mmol), potassium carbonate (K2CO3) (0.3 g, 2.1 mmol) and iodomethane (0.178 g, 1.2 mmol) in N,N-dimethylformamide (DMF) (10 mL) was stirred for 16 h at 0 °C and subsequently raised to room temperature. Upon completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (EtOAc) (2 x 20 mL). The organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) (20 mL) and brine (2 x 20 mL), dried over anhydrous sodium sulfate (Na2SO4) and concentrated to afford the target product methyl 5-bromo-6-chloronicotinate (61) (0.2 g, 94.7% yield).

29241-62-1 Synthesis

29241-62-1
244 suppliers
$5.00/250mg

74-88-4
360 suppliers
$15.00/10g

78686-77-8
211 suppliers
$6.00/1g

Yield:78686-77-8 94.7%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 16 h;

Steps:

10.1 Step 1: Methyl 5-bromo-6-chloronicotinate (61).

Step 1: Methyl 5-bromo-6-chloronicotinate (61). A mixture of 5-bromo-6- chloronicotinic acid 60 (0.2 g, 0.84 mmol), K₂C0₃ (0.3 g, 2.1 mmol) and methyl iodide (0.178 g, 1.2 mmol) in DMF (10 mL) was stirred for 16 h at RT. After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with saturated aqueous NaHC0₃ solution (20 mL), brine (2 x 20 mL) and dried (Na₂S0₄) and concentrated to afford ester 61 (0.2 g, 94.7%).

References:

WO2017/4608,2017,A1 Location in patent:Paragraph 0183

381247-99-0 Synthesis