Potassium Carbonate → Dimethyl 3-(4,5-Dimethoxy-2-(methoxymethoxy)phenyl)-4-(3,4-dimethoxyphenyl)-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dicarboxylate

HRID 1297197Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)=[C:14]([C:26]([O:28][CH3:29])=[O:27])[NH:13][C:12]=2[C:30]([O:32][CH3:33])=[O:31])=[C:5]([O:34][CH2:35][O:36][CH3:37])[CH:4]=1.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[CH2:43][CH2:44]Br.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.C(Cl)Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)=[C:14]([C:26]([O:28][CH3:29])=[O:27])[N:13]([CH2:44][CH2:43][C:42]3[CH:46]=[CH:47][C:48]([O:49][CH3:50])=[C:40]([O:39][CH3:38])[CH:41]=3)[C:12]=2[C:30]([O:32][CH3:33])=[O:31])=[C:5]([O:34][CH2:35][O:36][CH3:37])[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of 8 (297 mg, 0.58 mmol, 1.0 equiv), 3,4-dimethoxyphenethyl bromide (9,15 707 mg, 2.88 mmol, 5.0 equiv), and K2CO3 (398 mg, 2.88 mmol, 5 equiv) in DMF (5.8 mL) under Ar was warmed to 70° C. After 2.5 h, the mixture was cooled to 25° C. and solvent was removed in vacuo. Chromatography (SiO2, 3.5×15 cm, 20% EtOAc/CH2Cl2) provided 10 (372 mg, 94% yield) as a yellow oil: FABHRMS (NBA/NaI) m/z 702.2553 (M+Na+, C36H41NO12 requires 702.2526).

Workup

temperaturethe mixture was cooled to 25° C.
customsolvent was removed in vacuo

Sources & evidence

ORD record: ord-c9e82b9a72d7442682ef3c8b553c0ba0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250409B2

Reaction notes

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