Piperidine → (Z)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-5-(4,4, 5,5-tetramethyl-1,3,2-dioxab orolan-2-yl)indolin-3-ylidene)methyl)-1H-pyrrole-3-carboxamide

HRID 588280Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[O:3]1.[CH2:20]([N:22]([CH2:37][CH3:38])[CH2:23][CH2:24][NH:25][C:26]([C:28]1[C:32]([CH3:33])=[C:31]([CH:34]=O)[NH:30][C:29]=1[CH3:36])=[O:27])[CH3:21].N1CCCCC1>CCO>[CH2:37]([N:22]([CH2:20][CH3:21])[CH2:23][CH2:24][NH:25][C:26]([C:28]1[C:32]([CH3:33])=[C:31](/[CH:34]=[C:12]2\[C:13](=[O:18])[NH:14][C:15]3[C:11]\2=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:19])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:17][CH:16]=3)[NH:30][C:29]=1[CH3:36])=[O:27])[CH3:38]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (195 mg, 0.75 mmol) in EtOH (3 ml) was added N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (200 mg, 0.76 mmol) and piperidine (82 μL, 0.83 mmol). The mixture was stirred at 80° C. for 1 hour. After cooled down to room temperature, the reaction mixture was concentrated, filtrated, and washed with EtOH to give (Z)—N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-3-ylidene)methyl)-1H-pyrrole-3-carboxamide (218 mg) as yellow solid.

Workup

temperatureAfter cooled down to room temperature
concentrationthe reaction mixture was concentrated
filtrationfiltrated
washwashed with EtOH

Sources & evidence

ORD record: ord-d8b16a692ae744fdacaab30799d055d8
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227962B2

Reaction notes

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