Ethyl Acetate → HCID 86589703, compound

HRID 1444774Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].C[C:16]1[C:24](C)(C)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:27][C:28]([OH:30])=[O:29])[CH:22]=2)[N:17]=1.[Br-:31].[Na+].C(OCC)(=O)C>S1(CCCC1)(=O)=O>[Br-:31].[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][N+:17]1[C:18]2[C:23](=[CH:22][C:21]([CH2:27][C:28]([OH:30])=[O:29])=[CH:20][CH:19]=2)[CH2:24][CH:16]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

3,5-Dinitrobenzyl chloride (12.46 g, 57.5 mmol) was added to a solution of 2,3,3-trimethyl-3H-indol-5-yl-acetic acid (2.5 g, 11.5 mmol) with sodium bromide (5.92 g, 57.5 mmol) in sulfolan (10 ml). The reaction was heated at 100° C. for 20 hrs, then cooled to room temperature. The crude reaction mixture was added dropwise to an excess of ethyl acetate and the dark brown solid was filtered OFF and dissolved in dimethylsulfoxide before purification by reverse phase chromatography. The product was isolated as beige solid (54% yield). 1H NMR (d6-DMSO): δH: 8.75 (s, 1H), 8.45 (s, 2H), 7.15 (s, 1H), 6.95 (d, 1H), 6.70 (d, 2H), 5.10 (s, 2H), 3.95 (s, 2H), 3.45 (s, 3H), 1.40 (s, 6H). MALDI-TOF, m/z=398 (M+=398 for C20H20N3O6).

Workup

temperaturecooled to room temperature
customThe crude reaction mixture
filtrationthe dark brown solid was filtered OFF
dissolutiondissolved in dimethylsulfoxide before purification by reverse phase chromatography

Sources & evidence

ORD record: ord-d963380559a442ea9a4521d29c994e4f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662973B2

Reaction notes

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