Trifluoroacetic acid → 9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2193009Notes

Reaction equation

HRID 2193009 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[C:6]([C:15](C)([CH3:23])[C:16](OC(C)(C)C)=O)=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12](Cl)[N:11]=[CH:10][CH:9]=3.C(O)(C(F)(F)F)=[O:28]>ClCCl>[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[C:6]([CH:15]([CH3:23])[CH3:16])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:28])[C:13]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59375551Tert-butyl 2-(9-bromo-1-chlorobenzo[c]-1,6-naphthyridin-6-yl)-2-methylpropanoate

Product 1

HCID 593756889-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(9-bromo-1-chlorobenzo[c]-1,6-naphthyridin-6-yl)-2-methylpropanoate (3.32 g, 7.62 mmol) in dichloromethane (30 ml) was added TFA (30 ml). The solution was stirred for 12 hrs, then concentrated to a crude oil. EtOAc was added (20 mL), and the resulting solids were collected by vacuum filtration to afford 9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one. The filtrate was concentrated, EtOAc was added, and a second crop of product was obtained by vacuum filtration. 1H NMR (500 MHz, DMSO-D6) δ 11.91 (br d, 1H), 10.28 (d, 1H), 8.41 (d, 1H), 7.89 (dd, 1H), 7.58 (t, 1H), 6.77 (d, 1H), 4.05 (septet, 1H), 1.36 (d, 6H). LRMS (ESI) calc'd for (C15H13BrN2O) [M+H]+, 317.0; found 317.0.

Workup

  1. concentrationconcentrated to a crude oil
  2. additionEtOAc was added (20 mL)
  3. filtrationthe resulting solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-9971fa1108c44088908ed86964eaee84
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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