Sodium hydride → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

HRID 1427257Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.CCOC(C)=O>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:15]([N:1]2[C:9]3[C:4](=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1H-indole-4-carbaldehyde (2.0 g, 13.79 mmol) in DMF (50 mL) was added NaH (0.66 g, 16.55 mmol) at 0° C. After stirring for 30 min at 0° C., a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (4.67 g, 17.92 mmol) in DMF (20 mL) was added dropwise. The reaction was allowed to warm to rt and stirred for an additional 1 hr. Then it was diluted with EtOAc (200 mL) and quenched with water. The organic layer was separated and washed with brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-20% EtOAc/hexanes) to provide the title compound.

Workup

temperatureto warm to rt
stirringstirred for an additional 1 hr
customquenched with water
customThe organic layer was separated
washwashed with brine (50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was removed in vacuo
customThe residue was purified via column chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-8b48ad9519324559a723f178c789bb0c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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