Indole → HCID 11658322, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH:10](N(CC)C(C)C)([CH3:12])[CH3:11].C(Br)C#C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Zn+2].FC(F)(F)S([O-])(=O)=O>[CH2:12]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:10]#[CH:11]Participants
Procedure
To a solution of indole (0.50 g, 4.67 mmol), zinc trifluoromethanesulfonate (1.02 g, 2.8 mmol) and tetrabutylammonium iodide (0.86 g, 2.34 mmol) in toluene (14 mL) was added N,N-diisopropylethylamine (0.89 mL, 5.14 mmol) and the mixture was stirred at room temperature for about 15 min. Propargyl bromide (0.26 mL, 2.34 mmol) was added and the solution was stirred at room temperature for about 4 hours. The solution was quenched by addition of aqueous ammonium chloride and the mixture was extracted with diethyl ether. The combined organic extracts were dried (MgSO4), filtered and concentrated under vacuum, the residue was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (8:1) as the mobile phase to provide Example 650. 1H NMR (300 MHz, CDCl3) δ 2.13 (t, J=2.7 Hz, 1H), 3.70 (d, J=2.7 Hz, 2H), 6.55 (s, 1H), 7.37 (m, 2H), 7.64 (m, 2H), 7.98 (br s, 1H).
Workup
- stirringthe solution was stirred at room temperature for about 4 hours
- customThe solution was quenched by addition of aqueous ammonium chloride
- extractionthe mixture was extracted with diethyl ether
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
- customthe residue was purified by flash column chromatography on silica gel
- customto provide Example 650
Sources & evidence
- ORD record
- ord-633d3bdc652248d797ea781b88f0fbb5
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468371B2
Reaction notes
Loading…