Potassium Carbonate → 2-{[3'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-methyl-3-biphenylyl]methyl}-1H-isoindole-1,3(2H)-dione

温度

60 °C

Pd(OAc)2 (102.0 mg, 0.45 mmol, 0.03 eq.), PPh3 (476.4 mg, 1.82 mmol, 0.12 eq.), K2CO3 (3.14 g, 22.7 mmol, 1.50 eq.) and 2-[(3-bromo-5-methylphenyl)methyl]-1H-isoindole-1,3(2H)-dione (5.00 g, 13.1 mmol, 1.00 eq.) were suspended in anhydrous 1,4-dioxane (30 mL) under nitrogen. After the mixture was heated to 60° C. for 10 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (4.84 g, 18.2 mmol, 1.20 eq.) was added. Then the reaction mixture was stirred over night at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. Then water (25 mL) was added, extracted with CH2Cl2 twice (70 mL, 50 mL). The organic layer was washed with brine (20 mL×2), dried over anhydrous Na2SO4. After the solvent was removed, the crude product was purified on silica column chromatography, eluting with PE/EA (20:1 to 10:1), 4.2 g of product 2-{[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-methyl-3-biphenylyl]methyl}-1H-isoindole-1,3(2H)-dione was obtained, as a colorless liquid. Yield: 59%. 1H NMR (400 MHz, CDCl3): δ 0.11 (s, 6 H), 0.95 (s, 9 H), 2.38 (s, 3 H), 4.79 (s, 2 H), 4.87 (s, 2 H), 7.23 (s, 1 H), 7.31-7.49 (m, 6 H), 7.70-7.72 (m, 2 H), 7.84-7.86 (m, 2 H).

1. temperatureAfter cooled to room temperature
2. customthe solvent was removed under reduced pressure
3. additionThen water (25 mL) was added
4. extractionextracted with CH2Cl2 twice (70 mL, 50 mL)
5. washThe organic layer was washed with brine (20 mL×2)
6. dry with materialdried over anhydrous Na2SO4
7. customAfter the solvent was removed
8. customthe crude product was purified on silica column chromatography
9. washeluting with PE/EA (20:1 to 10:1)

ORDレコード

ord-e9744d4fe12c46ce9fa00e8eb27d6ce6

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08067408B2