N-methyl-2-pyrrolidone → HCID 86623628, compound

HRID 1821029Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:11][CH2:10]2)(=O)=O.[CH3:24][N:25]1CCCC1=O>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2]>[C:24]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:11][CH2:10]2)#[N:25]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl (5-trifluoromethylsulfonyloxy-6-methylindan-1-yl)acetate (405 mg, 1.15 mmol, from Step E) in N-methylpyrrolidinone (5 mL), Pd2dba3 (5.00 mg, 0.00546 mmol), dppf (7 mg, 0.0127 mmol) and Zn(CN)2 were added under Ar. The reaction mixture was heated to 100° C. for 15 hr, cooled to ambient temperature and diluted with EtOAc. The organic layer was washed several times with H2O, dried (brine, MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 afforded the 176 mg of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.71-1.90 (m, 1H), 2.36-2.60 (m, 5H), 2.71-2.82 (m, 1H), 2.82-2.96 (m, 2H), 3.55-3.68 (m, 1H), 3.76 (s, 3H), 7.11 (s, 1H), 7.47 (s, 1H).

Workup

temperaturecooled to ambient temperature
washThe organic layer was washed several times with H2O
dry with materialdried (brine, MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography (10% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record: ord-667e389690b5482785a890b9994a49c5
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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