Triethylamine → 4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one

温度

0 °C

To a solution of 4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one (1.12 g, 2.48 mmol) in anhydrous dichloromethane (25.0 mL) was added triethylamine (1.40 mL, 9.91 mmol) and SOCl2 (0.40 mL, 4.96 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h and quenched with water (30.0 mL). The organic layer was separated, washed with water (3×30.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give a gummy material. The residue was dissolved in acetic acid/tetrahydrofuran (3.00 mU22.0 mL) followed by the addition of zinc dust (0.81 g, 12.4 mmol) in one portion. The reaction mixture was stirred at ambient temperature for 16 h. After the solid was filtered, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with water (3×30.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to give the title compound (1.50 g, 77%) as a gummy material: MS (ES+) m/z 437.3 (M+1).

1. customquenched with water (30.0 mL)
2. customThe organic layer was separated
3. washwashed with water (3×30.0 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo to dryness
7. customto give a gummy material
8. stirringThe reaction mixture was stirred at ambient temperature for 16 h
9. filtrationAfter the solid was filtered
10. customthe solvent was removed in vacuo
11. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
12. washwashed with water (3×30.0 mL)
13. dry with materialdried over anhydrous sodium sulfate
14. filtrationfiltered
15. concentrationThe filtrate was concentrated in vacuo to dryness

ORDレコード

ord-c1e353a685594443a0d00d884e9b7e34

出典データセット

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07700641B2