Stannane, tributyl(1-ethoxyethenyl)- → Methyl (8-acetylquinolin-2-yl)(phenyl)carbamate

HRID 1055877Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]([O:8]CC)=[CH2:7])CCC.Br[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([N:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31](=[O:34])[O:32][CH3:33])[CH:26]=[CH:25]2>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.C1(C)C=CC=CC=1>[C:6]([C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([N:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31](=[O:34])[O:32][CH3:33])[CH:26]=[CH:25]2)(=[O:8])[CH3:7]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of Pd(PPh3)4 (60.8 mg, 0.053 mmol, Strem Chemicals, Newburyport, Mass.), tributyl(1-ethoxyvinyl)stannane (391 μl, 1.158 mmol, Sigma Aldrich), methyl (8-bromoquinolin-2-yl)(phenyl)carbamate (Example 46a; 376 mg, 1.053 mmol), and toluene (5.2 mL) were stirred under N2 at 100° C. for 20 h. Purification by column chromatography (silica gel: 0 to 10% EtOAc/hexanes followed by 70% EtOAc/hexanes) provided methyl (8-acetylquinolin-2-yl)(phenyl)carbamate, which was used without further purification in the next step. m/z (ESI, +ve) 349.1 (M+H)+.

Workup

customPurification by column chromatography (silica gel: 0 to 10% EtOAc/hexanes followed by 70% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c422b00f7ba54ddb9326e290bbbd8324
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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