Dimethylformamide → HCID 58447776, compound

HRID 592260Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][N:3]=1.[CH3:13][C:14]1[CH:19]=[C:18]([Sn](CCCC)(CCCC)CCCC)[CH:17]=[CH:16][N:15]=1.CN(C=O)C>C(OCC)(=O)C.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>[CH3:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][N:3]=2)[CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a flask containing methyl 2-(2-chloropyridin-4-yl)acetate 238-1 (1.00 g, 5.38 mmol), 2-methyl-4-(tributylstannyl)pyridine (2.06 g, 5.38 mmol), Pd(PPh3)4 (594 mg, 0.54 mmol.) under argon was added DMF (15 mL). The reaction mixture was stirred at 120° C. for 10 hours. After cooled to room temperature, the mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude was purified by silica gel flash chromatography, eluted with 5% methano in dichloromethane to give methyl 2-(2′-methyl-2,4′-bipyridin-4-yl)acetate 238-2 as dark orange oil. MS m/z 243.1 (M+1).

Workup

temperatureAfter cooled to room temperature
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness by rotary evaporation
customThe crude was purified by silica gel flash chromatography
washeluted with 5% methano in dichloromethane

Sources & evidence

ORD record: ord-fbd4360efdae435a928792fd790eada7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238646B2

Reaction notes

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