Br[C:2]1[C:3]2[CH:4]=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1.[CH3:19][Mg+].[Br-].[Li]CCCC.[CH3:27][S:28]SC.Cl>C1COCC1>[F:11][C:9]1[CH:10]=[C:2]([S:28][CH3:27])[C:3]2[CH:4]=[C:5]3[CH:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=1To 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.
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