Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=1.[F:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH2:27][CH2:28][NH2:29])=[CH:23][NH:24]2)=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH2:27][CH2:28][NH:29][C:11]([C:8]3[CH:7]=[C:6]([CH2:5][C:4]4[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=4)[O:10][N:9]=3)=[O:13])=[CH:23][NH:24]2)=[CH:20][CH:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the 5-(3-fluorobenzyl)isoxazole-3-carboxylic acid (0.057 g; 0.257 mmol), 2-(6-fluoro-1H-indol-3-yl)ethanamine (0.051 g; 0.284 mmol), HATU (0.108 g; 0.284 mmol) and N,N-diisopropylethylamine (0.112 mL; 0.649 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.040 g (41%) of the title compound as a white solid.
Workup
- customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
- washthe organic layer was washed with sodium carbonate, brine
- customdried
- concentrationconcentrated under reduced pressure
- customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-9298647cc310416583ecc891d6960b78
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Linked notes
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