Methyl Acrylate → methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

HRID 887756Notes

Reaction equation

Br[C:2]1[C:3]([C:23]([O:25][CH3:26])=[O:24])=[N:4][C:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:52]([O:56][CH3:57])(=[O:55])[CH:53]=[CH2:54]>CN(C)C=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:9]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[N:4]=[C:3]([C:23]([O:25][CH3:26])=[O:24])[C:2](/[CH:54]=[CH:53]/[C:52]([O:56][CH3:57])=[O:55])=[CH:7][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate (3.16 g, 7.68 mmol), palladium acetate (172 mg, 0.768 mmol), triphenylphosphine (404 mg, 1.54 mmol), potassium carbonate-(1.59 g, 11.5 mmol) and methyl acrylate (1.21 mL, 15.4 mmol) in N,N-dimethylformamide (77 mL) was stirred with heating at 120° C. for 12 hr. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (2.60 g, yield 81%).

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record: ord-aa8b62b95f7f40b28dabe8fd9b9a97e6
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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