Ethyl 5-formyl-4-methyl-1h-pyrrole-3-carboxylate → (Z)-5-(5-Fluoro-4-iodo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 366753

Reaction equation

[F:1][C:2]1[C:3]([I:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH2:13]([O:15][C:16]([C:18]1[C:22]([CH3:23])=[C:21]([CH:24]=O)[NH:20][CH:19]=1)=[O:17])[CH3:14]>N1CCCCC1.CC(O)C>[CH2:13]([O:15][C:16]([C:18]1[C:22]([CH3:23])=[C:21](/[CH:24]=[C:5]2\[C:6](=[O:11])[NH:7][C:8]3[C:4]\2=[C:3]([I:12])[C:2]([F:1])=[CH:10][CH:9]=3)[NH:20][CH:19]=1)=[O:17])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one (0.5 g, 1.8 mmol) (Example 2A) and 5-formyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (0.39 g, 2.17 mmol) (Example 116A above) in 1% piperidine in 2-propanol (6 mL) was heated at 80° C. for 3 h. The precipitate was collected and washed with water to give (Z)-5-(5-Fluoro-4-iodo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester. (Yield 0.67 g, 85%).

Workup

customThe precipitate was collected
washwashed with water

Sources & evidence

ORD record: ord-c6ed23c93cfd469f8ec129e52c6f8016
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130239

Linked notes

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