1-Methyl-1H-indole-3-carbaldehyde → HCID 58779044, compound
Reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[CH:4]=1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:16]([F:25])[C:15]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:25][C:16]1[C:15]2[O:2][C:1]([C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]([CH3:12])[CH:4]=3)=[N:13][C:14]=2[CH:19]=[CH:18][C:17]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22]Participants
Procedure
In methanol (50 ml), 3-formyl-1-methylindole (796 mg, 5.0 mmol), methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (1.0 g, 5.0 mmol) and Molecular Sieves 4A (10 g) were stirred at room temperature for 5 hours and then, at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and iodobenzene diacetate (5.0 mmol) was added thereto. After stirring at room temperature for 14 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions, methyl 7-fluoro-2-(1-methyl-3-indolyl)-6-benzoxazolylacetate (860 mg, including impurities) was obtained as a pale brown solid. The compound was provided for the subsequent reaction without further purification.
Workup
- distillationthe reaction mixture was distilled under reduced pressure
- customto remove the solvent
- customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions
Sources & evidence
- ORD record
- ord-99c7543ef46a426badce607a261086ba
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157487B2
Reaction notes
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