1,1'-Thiocarbonyldi-2(1H)-pyridone → 8-Bromo-5-fluoro-3-isothiocyanatoisoquinoline

HRID 1876038

Reaction equation

HRID 1876038 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH2:12])=[CH:7]2.[C:14](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:15]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([N:12]=[C:14]=[S:15])=[CH:7]2

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 534189908-Bromo-5-fluoroisoquinolin-3-amine

Product 1

HCID 592866428-Bromo-5-fluoro-3-isothiocyanatoisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-bromo-5-fluoroisoquinolin-3-amine (0.30 g, 1.245 mmol) and dichloromethane (5 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.318 g, 1.369 mmol). The resulting mixture was stirred at rt for 3 hours. The product was directly purified on a 40 g Thompson silica cartridge (3% to 100% EtOAc in Hexanes, 1200 mL). The desired product was obtained as a off-white solid (0.23 g, 0.812 mmol, 65.3% yield). LC/MS (2.098 min, MH+: 284.93). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.38 (1H, s), 8.04 (1H, dd, J=8.31, 4.78 Hz), 7.96 (1H, s), 7.67 (1H, dd, J=9.82, 8.31 Hz). 19F NMR (376 MHz, DMSO-d6) δ ppm −122.13 (1F, s).

Workup

  1. customThe product was directly purified on a 40 g Thompson silica cartridge (3% to 100% EtOAc in Hexanes, 1200 mL)

Sources & evidence

ORD record
ord-58b9eca935ce48048dc69746eaffe5a3
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Linked notes

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