Hydrochloric Acid → HCID 67072424, compound

HRID 1969434Notes

Reaction equation

HRID 1969434 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([O:23]CC)=[O:22])=[CH:6][N:7]2[CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1.N1C2C=CC=CC=2NC=1.O[C:37]1[CH:38]=[CH:39][CH:40]=[C:41]2[C:46]=1[N:45]=[CH:44][CH:43]=C2.C(=O)([O-])[O-].[Cs+].[Cs+].[Al].Cl>CS(C)=O.[OH-].[Li+].[Cu]I>[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([OH:23])=[O:22])=[CH:6][N:7]2[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([N:45]2[C:46]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:43]=[CH:44]2)=[CH:18][CH:19]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 5798BenzimidazoleHCID 10796Cesium carbonateHCID 5359268AluminumHCID 58297067HCID 58297067, compound

Product 1

HCID 67072424HCID 67072424, compound

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of ethyl 5,8-difluoro-1-(4-iodobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.200 g, 0.426 mmol) and benzimidazole (0.252 g, 2.13 mmol) in 3 mL of dimethylsulfoxide under nitrogen was added 8-hydroxyquinoline (0.013 g, 0.085 mmol), 1 N cesium carbonate (0.852 mL, 0.852 mmol), and copper(I)iodide (0.041 g, 0.21 mmol). The reaction vessel was covered with aluminum foil and heated to 95° C. for 24 hours. The reaction mixture was cooled to room temperature, and saturated aqueous lithium hydroxide (20 drops) was added. After 10 hours, 6 N HCl was added to pH ˜4. The reaction mixture was filtered and purified via reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 432.1 for M+H+. 1H NMR (400 MHz, d6-DMSO) δ 9.21 (s, 1H), 7.84-7.70 (m, 2H), 7.67 (d, J=8.2 Hz, 2H), 7.62 (bs, 1H), 7.43 (m, 3H), 7.32-7.26 (m, 3H), 5.99 (d, J=3.5 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-feec78a91fc6419fa7b00e96a89b4f47
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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