2-chloro-4-(thiophen-2-yl)pyridine synthesis

6synthesis methods

Product Name:2-chloro-4-(thiophen-2-yl)pyridine
CAS Number:1289555-51-6
Molecular formula:C9H6ClNS
Molecular Weight:195.67

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6165-68-0 Synthesis

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Yield:1289555-51-6 88%

Reaction Conditions:

with sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride in tetrahydrofuran;water at 70;

Steps:

113.1

Step 1 A round-bottomed flask was charged with 2-chloro-4-iodopyridine (600 mg, 2.5 mmol), thiophen-2-ylboronic acid (385 mg, 3.0 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (176 mg, 0.251 mmol), THF (9 mL) and 2M aqueous sodium carbonate (3.0 mL, 6.0 mmol). The reaction mixture was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature then diluted with 20 mL water and extracted with 100 mL EtOAc (2*). The combined organic layers were washed with 20 mL water and 20 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on ~2 g SiO₂ and chromatographed over 24 g SiO₂ with EtOAc/hexanes (gradient: 0-10% EtOAc). All fractions containing product were combined and concentrated to give 430 mg (88%) of 2-chloro-4-thiophen-2-yl-pyridine as a light yellow solid.

References:

US2011/230462,2011,A1 Location in patent:Page/Page column 98

1003-09-4 Synthesis