Methanol → HCID 24823730, compound

HRID 1925368Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1.CN([CH:34]=[O:35])C.[CH3:36][OH:37]>CC(O)=O.CC(O)=O.[Pd]>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([C:36]([O:35][CH3:34])=[O:37])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The following reagents were placed in a glass jacket inside of a Parr bomb: 4-chloro-7-methoxyquinoline (2 g, 10.33 mmol), Pd(OAC)2 (225 mg, 1.0 mmol), 1,3-diphenylphosphino propane [DPPE] (618 mg, 1.55 mmol), DMF (15 mL), MeOH (3 mL) and TEA (2.87 mL, 20.66 mmol) and the vessel sealed. The vessel was pressurized to 50 psi CO and stirred at 70° C. (internal temperature) for 19 h. The vessel was allowed to cool to RT, carefully opened and the contents transferred to a round bottom flask and concentrated in-vacuo. A solution of 2:1 EtOAc:hexanes was added to the residual solid and the solid filtered (and discarded). The filtrate was evaporated and the residue purified by column chromatography using a mixture of EtOAc/hexanes as the eluent. The title compound was obtained as a yellow solid.

Workup

temperatureto cool to RT
customthe contents transferred to a round bottom flask
concentrationconcentrated in-vacuo
additionA solution of 2:1 EtOAc:hexanes was added to the residual solid
filtrationthe solid filtered (and discarded)
customThe filtrate was evaporated
customthe residue purified by column chromatography
additiona mixture of EtOAc/hexanes as the eluent

Sources & evidence

ORD record: ord-d819ae2a85e84003bd635448ec4a7be5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

Loading…