1,1'-Thiocarbonyldi-2(1H)-pyridone → 7-Bromo-3-isothiocyanatoisoquinoline

HRID 250137Notes

Reaction equation

HRID 250137 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[Br:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[C:23]([NH2:28])[N:24]=[CH:25]2)=[CH:20][CH:19]=1.BrC1C=CC=C2C=1C=C(N)N=C2>ClCCl>[Br:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[C:23]([N:28]=[C:1]=[S:2])[N:24]=[CH:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 529877577-Bromoisoquinolin-3-amineHCID 534184475-Bromoisoquinolin-3-amine

Product 1

HCID 574766077-Bromo-3-isothiocyanatoisoquinolineYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one 1.145 g, 4.93 mmol) in dichloromethane at room temperature was added the mixture of 7-bromoisoquinolin-3-amine and 5-bromoisoquinolin-3-amine from step B (1.0 g, 4.5 mmol). The orange solution was stirred at room temperature for 18 hours. LCMS indicated the formation of product. The deep orange solution was purified by silica gel chromatography (0-5% ethyl acetate-hexanes). The first product fractions were combined and concentrated in vacuo to afford 7-bromo-3-isothiocyanatoisoquinoline (0.27 g, 0.377 mmol, 22% yield) as a yellow solid. 1H NMR (400 MHz, Acetone) δ ppm 9.19 (1H, s), 8.41 (1H, s), 7.86-8.02 (2H, m), 7.76 (1H, s). R.T.=4.28; [M+H]+=267.04. The second product fractions were combined and concentrated in vacuo to afford 5-bromo-3-isothiocyanatoisoquinoline (0.25 g, 0.377 mmol, 21% yield) as a yellow solid. 1H NMR (400 MHz, Acetone) δ ppm 9.24 (1H, s), 8.23 (1H, d), 8.15 (1H, d), 7.81 (1H, s), 7.64 (1H, t). LCMS:R.T.=4.61; [M+H]+=267.04.

Workup

  1. customThe deep orange solution was purified by silica gel chromatography (0-5% ethyl acetate-hexanes)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4fce31f535e419a9c44a81e32ef6c15
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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