Sodium hydride → Ethyl3-Formyl-2-isopropyl-1-(oxazol-2-ylmethyl)-1H-indole-6-carboxylate

HRID 40064Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:18]=[O:19])=[C:11]([CH:15]([CH3:17])[CH3:16])[NH:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].Cl[CH2:23][C:24]1[O:25][CH:26]=[CH:27][N:28]=1>CN(C=O)C.CCOC(C)=O>[CH:18]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[N:12]([CH2:23][C:24]2[O:25][CH:26]=[CH:27][N:28]=2)[C:11]=1[CH:15]([CH3:16])[CH3:17])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate (Compound 34, 1.22 g, 4.72 mmol) in DMF (10 ml) was added NaH (170 mg, 7.08 mmol) and 2-(chloromethyl)oxazole (1.10 g, 9.44 mmol). The reaction was stirred at 25° C. for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a yellow oil.

Workup

washwashed with H2O, brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record: ord-621e0def98824858a359ec5271016cbe
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524917B2

Reaction notes

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