Hydrochloric Acid → (+/-)-Methyl [6-fluoro-8-(methylthio)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

Temperature

-78 °C

To a solution of (+/−)-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (Example 7A, Step 1, 400 mg, 1.3 mmol) in THF (10 mL) at −78° C. was added 3M MeMgBr (1.5 mmol) followed by the addition of n-BuLi (2.6 mmol, 1.6M solution). The reaction mixture was stirred at −78° C. for 5 minutes and an excess of methyl disulfide (300 mg) was added. The reaction mixture was warmed to r.t. and stirred for 15 minutes and 1N HCl was added. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was dissolved in THF and the solution was cooled to 0° C. and treated with an excess of CH2N2. The reaction mixture was stirred for 5 minutes and the solvent removed to give 380 mg of the title compound as a pale yellow syrup used as such.

1. temperatureThe reaction mixture was warmed to r.t.
2. stirringstirred for 15 minutes
3. customThe phases were separated
4. extractionthe aqueous layer was extracted with EtOAc
5. dry with materialThe combined organic layers were dried over Na2SO4
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in THF
8. temperaturethe solution was cooled to 0° C.
9. additiontreated with an excess of CH2N2
10. stirringThe reaction mixture was stirred for 5 minutes
11. customthe solvent removed

ORD record

ord-e3f7a60f619b4e8ea1ffb95fdc87c4e0

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144913B2