HCID 67057700, compound → HCID 67057701, compound

HRID 604634Notes

Reaction equation

[F:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([C:15](=[O:20])[CH2:16][CH2:17]3)=[CH:13][C:12]=2[C:21]([O:23][CH3:24])=[O:22])=[C:4]([O:25][CH3:26])[CH:3]=1.[CH3:27][Mg]Cl>CCCCCCC.C1COCC1>[F:1][C:2]1[C:7]([CH:8]([CH3:9])[CH3:10])=[CH:6][C:5]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([OH:20])([CH3:27])[CH2:16][CH2:17]3)=[CH:13][C:12]=2[C:21]([O:23][CH3:24])=[O:22])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-oxoindane-5-carboxylate (45.9 mg, 0.129 mmol) in heptane (1 mL) and THF (1 mL) at −20° C. under N2, was added dropwise 3N MeMgCl in THF (86 uL, 0.258 mmol). The reaction mixture was stirred at −20° C. for 2 h. The mixture was quenched with sat. aq. NH4Cl and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give methyl 6-(4-fluoro-5-isopropyl-2-methoxyphenyl)-3-hydroxy-3-methylindane-5-carboxylate. LCMS calc.=395.2; found=394.9 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 7.89 (s, 1H); 7.20 (s, 1H); 7.09 (d, J=8.6 Hz, 1H); 6.62 (d, J=12.1 Hz, 1H); 3.72 (s, 3H); 3.70 (s, 3H); 3.28-3.20 (m, 1H); 3.15-3.09 (m, 1H); 2.96-2.90 (m, 1H); 2.36-2.24 (m, 2H); 1.91 (br s, 1H); 1.66 (s, 3H); 1.30 (d, J=6.9 Hz, 6H).

Workup

customThe mixture was quenched with sat. aq. NH4Cl
extractionextracted with EtOAc (3×)
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-32981597cb1444bcbd0cb8a1a5d9fc85
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910592B2

Reaction notes

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