Water → Methyl 1-methyl-3-phenyl-1H-indole-6-carboxylate

HRID 409909Notes

Reaction equation

[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:22]I.O>CN(C=O)C>[CH3:22][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (60% dispersion in mineral oil, 4.52 mmol, 186 mg) was added portion-wise to a solution of methyl 3-phenyl-1H-indole-6-carboxylate (2.07 mmol, 757 mg) in DMF at 0° C. and the mixture was stirred for 20 min. Methyl iodide (2.28 mmol, 0.14 mL) was added and the reaction mixture was maintained at 0° C. for 1 h. Water was then added and the reaction was extracted with EtOAc. The organics were concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give 16c.

Workup

extractionthe reaction was extracted with EtOAc
concentrationThe organics were concentrated
custompurified by flash column chromatography (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-be4aad3cc39d424887ed63191d43d9b5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759533B2

Reaction notes

Loading…