Ethyl Acetate → HCID 67067828, compound

HRID 1037390Notes

Reaction equation

[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](=[O:39])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]3[N:34]([CH3:38])[N:35]=[C:36](I)[C:23]3=[CH:22][CH:21]=4)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:41][CH2:42]OC(C)=O>C1(C)C=CC=CC=1.C1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](=[O:39])[C:20]4[C:25]([O:26][C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]3[N:34]([CH3:38])[N:35]=[C:36]([CH:41]=[CH2:42])[C:23]3=[CH:22][CH:21]=4)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of {1-[4-(3-iodo-1-methyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (27 mg, 0.0417 mmol), tetrakis(triphenylphosphine)palladium(0) (4.8 mg, 0.004 mmol) and vinyltributylin (0.0183 mL, 0.063 mmol) in toluene (2 mL) was stirred at 90° C. under nitrogen. After 3 hours, reaction mixture cooled to RT and was subjected to flash chromatography (SiO2, gradient 20 to 40% EtOAc in cyclohexane) to afford the title compound (23.4 mg) as a yellow gum. LCMS (Method H): RT=4.67 min, [M+H]+=548.

Workup

customreaction mixture
temperaturecooled to RT

Sources & evidence

ORD record: ord-ccd82e9342cf49b385b2772167b7533e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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