تفاعل #74662

معادلة التفاعل

sodium carbonate

4-chloro-2-iodoanisole

2-chloropyridine-4-boronic acid

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title compound

2-Chloro-4-(5-chloro-2-methoxyphenyl)pyridine

المذيبات

ethylene glycol dimethyl ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةFollowing LCMS analysis the reaction was warmed to 75° C.
2. 2
   workup.STIRRINGstirred for 5 hours
3. 3
   درجة الحرارةbefore cooling to room temperature
4. 4
   أخرىThe reaction was partitioned between ethyl acetate (100 mL)
5. 5
   غسيلThe organic layer was washed with water (50 mL)
6. 6
   تجفيفdried over anhydrous magnesium sulphate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvents removed in vacuo
9. 9
   أخرىto give the crude product as an orange oil (2.95 g)
10. 10
    أخرىThe material was purified
11. 11
    غسيلan ISCO™ companion (120 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate)
12. 12
    workup.ADDITIONFractions containing product
13. 13
    تركيزconcentrated in vacuo

الإجراء التجريبي

To a nitrogen purged aqueous solution of sodium carbonate (2M, 14 mL) and ethylene glycol dimethyl ether (25 mL) was added 4-chloro-2-iodoanisole (2.50 g, 0.00931 mol), 2-chloropyridine-4-boronic acid (1.61 g, 0.0102 mol) and bis(triphenylphosphine)palladium (II) dichloride (327 mg, 0.00047 mol). The reaction mixture was warmed to 50° C. and stirred for 5 hours. Following LCMS analysis the reaction was warmed to 75° C. and stirred for 5 hours before cooling to room temperature. The reaction was partitioned between ethyl acetate (100 mL) and a 10% w/v aqueous solution of citric acid (50 mL). The organic layer was washed with water (50 mL), dried over anhydrous magnesium sulphate, filtered and the solvents removed in vacuo to give the crude product as an orange oil (2.95 g). The material was purified using an ISCO™ companion (120 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as an off white solid (1.10 g).

المصدر