5-fluoro-1-methyl-1H-indole-3-carbaldehyde → HCID 86592802, compound

HRID 1372763Notes

Reaction equation

HRID 1372763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH:12]=[O:13].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[O:13][C:16]2[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 13820095-fluoro-1-methyl-1H-indole-3-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Product 1

HCID 86592802HCID 86592802, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (25 ml), 5-fluoro-1-methylindole-3-carbaldehyde (989 mg, 5.58 mmol) and methyl 4-amino-3-hydroxyphenylacetate (1.27 g, 6.99 mmol) were stirred at room temperature for 9 hours. Iodobenzene diacetate (2.16 g, 6.69 mmol) was added and the mixture was stirred further at room temperature for 18 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue thus obtained was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:2, v/v) eluate fractions, a mixture (933 mg) of methyl (2-(5-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl)acetate and 5-fluoro-1-methylindole-3-carboxaldehyde was obtained as a red solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue thus obtained
  4. customwas purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (1:2

Sources & evidence

ORD record
ord-9aa5af1fd7564faaa252af7387d1427c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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