1,1'-Thiocarbonyldi-2(1H)-pyridone → 2'-Isothiocyanato-2-methoxy-3,4'-bipyridine

HRID 250124Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[N:15]([C:11]1[CH:10]=[C:9]([C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:13][N:12]=1)=[C:16]=[S:17]

Participants

Conditions

Temperature: 40 °C

Procedure

To 2-methoxy-3,4′-bipyridin-2′-amine (0.53 g, 2.63 mmol) in dichloromethane (20 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.62 g, 2.7 mmol) and the reaction mixture was stirred at 40° C. for 4 hours. The reaction was cooled to room temperature and chromatographed (Biotage: 10-100% ethyl acetate/hexanes) to yield 2′-isothiocyanato-2-methoxy-3,4′-bipyridine (0.46 g, 1.9 mmol, 71.8% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 8.67 (d, J=2.44 Hz, 1 H), 8.26 (dd, J=4.88, 1.53 Hz, 1 H), 8.15 (dd, J=8.24, 2.44 Hz, 1 H), 7.89 (dd, J=7.32, 1.53 Hz, 1 H), 7.48 (d, J=8.24 Hz, 1 H), 7.15 (dd, J=7.32, 4.88 Hz, 1 H), 3.91 (s, 3 H). MS (LC/MS) R.T.=2.87; [M+H]+=244.9.

Workup

temperatureThe reaction was cooled to room temperature
customchromatographed (Biotage: 10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-446f004964e74a7f87345ede753cb217
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863291B2

Reaction notes

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