Methyl Acrylate → HCID 67358524, compound

HRID 404314Notes

Reaction equation

[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([C:44](Br)=[CH:45][N:46]=1)[C:40]([O:42][CH3:43])=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CN1C(=O)CCC1>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([C:44]([CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4])=[CH:45][N:46]=1)[C:40]([O:42][CH3:43])=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To NMP (1 mL) was added methyl acrylate (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), tri-o-tolylphosphine (8.5 mg, 28 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and palladium diacetate (2.5 mg, 11 μmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA). The solution was degassed three time with nitrogen. To this solution was then added a 1 mL NMP solution of methyl 2-(benzyloxy)-5-bromoisonicotinate (120 mg, 372 μmol). The reaction was stirred at 90° C. overnight and then purified by column chromatography (silica gel, 10% EtOAc/hexane) to give desired product H6.2 (50.2 mg, 41.4%). MS ESI (pos.) m/e: 328.1 (M+H)+.

Workup

customThe solution was degassed three time with nitrogen
custompurified by column chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record: ord-3fadcda8fa664b7ea5548b4ca11e97a3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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