Toluene → HCID 75231051, compound

HRID 2078397Notes

Reaction equation

C1(C)C=CC=CC=1.[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([CH:15]=[N:16][C:17]([O:19][Si](C)(C)C)=[CH2:18])[CH:14]=1.C(OC([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=2)/[C:34](=[CH:42]/[C:43]2[C:44]([O:50][C:51]([C:54]([O:56][CH3:57])=[O:55])([CH3:53])[CH3:52])=[N:45][CH:46]=[C:47]([Cl:49])[CH:48]=2)/[C:33]1=[O:58])=O)(C)(C)C>CO>[Cl:41][C:38]1[CH:39]=[C:40]2[NH:32][C:33](=[O:58])[C:34]3([CH:42]([C:43]4[C:44]([O:50][C:51]([C:54]([O:56][CH3:57])=[O:55])([CH3:53])[CH3:52])=[N:45][CH:46]=[C:47]([Cl:49])[CH:48]=4)[CH2:19][C:17](=[O:18])[NH:16][CH:15]3[C:13]3[CH:14]=[C:9]([F:8])[CH:10]=[CH:11][C:12]=3[CH3:24])[C:35]2=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a toluene solution (50 mL) of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (18 mmol) was added E/Z-6-chloro-3-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-pyridin-3-ylmethylene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (3 g, 6 mmol). Then the reaction mixture were heated at 130° C. for 2 h. After the solution was cooled to room temperature, methanol was added, and then the mixture was concentrated. Then a mixture of trifluoroacetic acid (10 mL) and dichloromethane (30 mL) was added. The reaction mixture was stirred at room temperature for 10 min. The solution was concentrated and the residue was purified by Prep-HPLC to give title compound as a white solid (170 mg).

Workup

temperatureAfter the solution was cooled to room temperature
concentrationthe mixture was concentrated
additionThen a mixture of trifluoroacetic acid (10 mL) and dichloromethane (30 mL)
additionwas added
concentrationThe solution was concentrated
customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record: ord-426138b7bf014f07b1bc01684fe58d7d
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928233B2

Reaction notes

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