Selenious Acid → 5-Chloro-4-ethoxycarbonylmethyl-2-formyl-indole-1-carboxylic acid methyl ester

HRID 1161887

Reaction equation

[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:21])=[O:4].[Se](O)(O)=[O:23]>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:21]=[O:23])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-4-ethoxycarbonylmethyl-2-methyl-indole-1-carboxylic acid methyl ester (398 mg, 1.28 mmol) is dissolved under an atmosphere of argon in dioxane (18 ml). Selenious acid (331 mg, 2.56 mmol) is added, and the reaction mixture is heated to 100° C. for 18 hours. TLC analysis indicates complete conversion of the starting material. The reaction mixture is diluted with EtOAc and poured on water. The organic layer is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated. The solid residue is purified by FCC (hexane/EtOAc 2:1) to afford the title compound. 1H NMR (DMSO, 400 MHz) δ 1.20 (t, J=6.6 Hz, 3H), 4.09 (s, 3H), 4.12 (q, J=6.6 Hz, 2H), 4.19 (s, 2H), 7.64 (d, J=10.8, 1H), 8.09 (d, J=10.8, 1H), 10.32 (s, 1H); ES-MS: 346.1.1 [M+Na]+.

Workup

additionpoured on water
washThe organic layer is washed with saturated aqueous NaCl solution
dry with materialdried over Na2SO4
concentrationconcentrated
customThe solid residue is purified by FCC (hexane/EtOAc 2:1)

Sources & evidence

ORD record: ord-8fa564b97d724679a1570eb4d623a91f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820672B2

Linked notes

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