Cesium carbonate → HCID 58168002, compound

HRID 1029279Notes

Reaction equation

HRID 1029279 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Br[CH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([O:24][CH3:25])=[O:23].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:1][CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24][CH3:25])=[O:23])=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168002HCID 58168002, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 (171 mg, 0.81 mmol), methyl 3-(bromomethyl)benzoate (0.01 mL, 0.97 mmol), and Cs2CO3 (791 mg, 2.43 mmol) were suspended in DMF (3 mL), and stirred overnight at ambient temperature. The reaction solution was purified directly via flash chromatography on silica gel to provide 458 (130 mg, 44% yield) as a white powder. LC-MS (M+H=360, obsd.=360). 1H NMR (400 MHz, DMSO-D6) δ 8.53 (dd, J=6.3, 11.9, 2H), 8.06 (d, J=8.7, 1H), 7.86 (s, 1H), 7.80 (d, J=8.0, 1H), 7.56 (d, J=7.6, 1H), 7.44 (d, J=8.5, 2H), 7.31 (m, 1H), 6.91 (d, J=9.0, 1H), 6.22 (s, 1H), 5.71 (s, 2H), 3.80 (s, 3H).

Workup

  1. customThe reaction solution was purified directly via flash chromatography on silica gel

Sources & evidence

ORD record
ord-2bcf490e793f480ca889e89d339ef680
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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