1,2-Dichloroethane → 5-[(1H-Indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]([OH:16])=O)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:4].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:38]1[C:46]2[C:41](=[C:42]([CH2:47][NH2:48])[CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14](=[O:16])[NH:48][CH2:47][C:42]2[CH:43]=[CH:44][CH:45]=[C:46]3[C:41]=2[CH:40]=[CH:39][NH:38]3)=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:4]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-Trifluoromethyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (570 mg, 2.24 mmol) in anhydrous DMF (10 mL) was added triethylamine (1.25 mL, 8.96 mmol), EDC (520 mg, 2.69 mmol), HOBT (360 mg, 2.69 mmol), and C-(1H-Indol-4-yl)-methylamine (390 mg, 2.69 mmol). The mixture was stirred at room temperature 3 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-70% EtOAc in hexane to afford the desired product (0.27 g, 31% yield).
Workup
- customquenched
- additionby pouring into EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography with 0-70% EtOAc in hexane
Sources & evidence
- ORD record
- ord-e1ca80035e7748fbbae440ed41d9c92f
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404859B2
Reaction notes
Loading…