Potassium Carbonate → HCID 67334703, compound

HRID 1804823Notes

Reaction equation

[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:30])=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26].C(Cl)Cl.CO>CN(C=O)C>[F:30][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH:3]=[N:2]2)=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of cinnolin-4(1H)-one in DMF (0.1 M) was added K2CO3 (1.2 eq) and methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 A1, 1 eq). The mixture was stirred and heated to 100° C. for 1 h. After cooling to RT the solvent was removed under reduced pressure and the residue was partitioned between DCM and H2O. The organic phase was washed with brine, dried (Na2SO4) and filtered and the solvent was removed under reduced pressure. The product was isolated by flash chromatography on silicagel, using a gradient of DCM/MeOH (from 0% to 10% MeOH in 10 CV). The 2-[4-fluoro-3-(methoxycarbonyl)benzyl]cinnolin-2-ium-4-olate was eluted after the title compound.

Workup

temperatureAfter cooling to RT the solvent
customwas removed under reduced pressure
customthe residue was partitioned between DCM and H2O
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe product was isolated by flash chromatography on silicagel
washThe 2-[4-fluoro-3-(methoxycarbonyl)benzyl]cinnolin-2-ium-4-olate was eluted after the title compound

Sources & evidence

ORD record: ord-7a3413cbba1f4dceb9d1222b435bceec
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354413B2

Reaction notes

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