反应详情

1.0 M NaOH in water (5 mL, 5 mmol) was added to a solution of 2-bromo-5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine trifluoroacetate (0.268 g, 0.552 mmol, from Step 1) in THF (5 mL) and methanol (5 mL) and the reaction was stirred for 1 hour. Water was added and THF and MeOH were removed in vacuo. The product was extracted with EtOAc. The extracts were dried over sodium sulfate, filtered and concentrated. A solution of this residue in DMF (3 mL) was treated with K2CO3 (0.23 g, 1.6 mmol) and benzyl bromide (0.0656 mL, 0.552 mmol, Aldrich). After stirring overnight, the reaction was partitioned between water and ethyl acetate and extracted a total of three times. The combined extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-30% EtOAc in hexanes to afford product as a white crystalline solid. Yield: (177 mg, 99%).

1. customTHF and MeOH were removed in vacuo
2. extractionThe product was extracted with EtOAc
3. dry with materialThe extracts were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. stirringAfter stirring overnight
7. customthe reaction was partitioned between water and ethyl acetate
8. extractionextracted a total of three times
9. dry with materialThe combined extracts were dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe product was purified by flash chromatography
13. washeluting with a gradient from 0-30% EtOAc in hexanes
14. customto afford product as a white crystalline solid