تفاعل #614750

معادلة التفاعل

spiro[1-benzofuran-3,1′-cyclopropan]-4-ol

Intermediate 85

spiro[1-benzofuran-3,1′-cyclopropan]-4-ol

N,N-dimethylformamide

2-chloro-5-nitropyridine

→

title compound

المردود 81.5%

5-nitro-2-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)pyridine

المردود 81.5%

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with brine (1 ml)
2. 2
   workup.ADDITIONdiluted with water (2 ml)
3. 3
   استخلاصextracted with ethyl acetate (3×10 ml)
4. 4
   تجفيفThe organic layer was dried over sodium sulphate
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents

الإجراء التجريبي

To a solution of spiro[1-benzofuran-3,1′-cyclopropan]-4-ol (Intermediate 85, 70 mg) in dry N,N-dimethylformamide (2 ml) potassium carbonate (89 mg, 0.647 mmol) and then 2-chloro-5-nitropyridine (75 mg, 0.475 mmol) were added and the reaction mixture was stirred for 3 hours at 100° C. The reaction was quenched with brine (1 ml), diluted with water (2 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents affording the title compound as a white solid (100 mg).

المصدر