Acetate → (+/-)-[9-[(4-CHLOROPHENYL)THIO]-6-FLUORO-8-(2-METHYLPHENYL)-2,3-DIHYDRO-1H-PYRROLO[1,2-a]INDOL-1-YL]ACETIC ACID

Temperature

80 °C

To (+/−)-methyl[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate (Example 7, Step 9, 100 mg, 0.21 mmol) in 1-propanol (2 mL) were added 2-methylphenylboronic acid (57 mg, 0.42 mmol), 3:1 mixture of triphenylphosphine/palladium (>) acetate (11 mg) and 2M aqueous potassium carbonate (0.3 mL). The mixture was degassed and stirred at 80° C. for 6 h and the reaction mixture was cooled to r.t. Then THF (3 mL) and 1N LiOH were added and the mixture was stirred for 2 h at r.t. AcOH (0.5 mL) and brine were added and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 40% EtOAc/hexane containing 1% AcOH to give 90 mg of the title compound.

1. customThe mixture was degassed
2. temperaturethe reaction mixture was cooled to r.t
3. additionThen THF (3 mL) and 1N LiOH were added
4. stirringthe mixture was stirred for 2 h at r.t
5. additionAcOH (0.5 mL) and brine were added
6. extractionthe aqueous layer was extracted with EtOAc
7. dry with materialThe combined organic layers were dried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluted with 40% EtOAc/hexane containing 1% AcOH

ORD record

ord-85dd169599e140d1b547256cdc85ecdd

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144913B2