HCID 59442007, compound → HCID 59441667, compound

HRID 1014181Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][N:16](CC=C)[CH2:15][CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]>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([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][NH:16][CH2:15][CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 35 °C

Procedure

Nitrogen was bubbled through dichloromethane (100 mL) for 10 minutes followed by the addition of N-dimethylbarbituric acid (15.4 g, 98.4 mmol) and Pd(PPh3)4 (1.9 g, 1.6 mmol). After the addition of 5-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)-1,2,3,6-tetrahydropyridine, the reaction was heated to 35° C. and stirred for 3 h. To the cooled solution was added saturated aq. Na2CO3 (100 mL), and the mixture was allowed to stir at RT for 30 min. After extraction with dichloromethane (2×50 mL), drying (Na2SO4), and concentration, chromatography on SiO2 afforded 5-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (5.3 g, 70% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.31 (d, J=4.0 Hz, 2 H), 3.02 (t, J=5.7 Hz, 2 H), 3.29 (s, 1H), 3.71 (d, J=1.8 Hz, 2 H), 3.97 (s, 3 H), 6.32 (t, J=4.0 Hz, 1 H), 6.95 (d, J=8.4 Hz, 1H), 6.98 (s, 1 H), 7.85 (d, J=8.4 Hz, 1 H).

Workup

customNitrogen was bubbled through dichloromethane (100 mL) for 10 minutes
stirringto stir at RT for 30 min
extractionAfter extraction with dichloromethane (2×50 mL)
customdrying
concentration(Na2SO4), and concentration, chromatography on SiO2

Sources & evidence

ORD record: ord-5afb611d11564c4492bc47472ce595eb
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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