Methanol → HCID 117737033, compound

HRID 1504478Notes

Reaction equation

HRID 1504478 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([C:29]#[N:30])[C:26]([Br:31])=[CH:25][C:24]=2[O:32][CH3:33])=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C[O-].[Na+]>C(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:22]([C:23]1[C:24]([O:32][CH3:33])=[CH:25][C:26]([Br:31])=[C:27]([CH:28]=1)[C:29]#[N:30])[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 117746867HCID 117746867, compound

Product 1

HCID 117737033HCID 117737033, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-cyano-2-methoxyphenyl)amino)phenyl)acrylate (963 mg, 1.840 mmol) and MeOH (9199 μl) to give a thick, yellow suspension. Sodium methoxide (25 wt % in MeOH) (80 μl, 0.368 mmol) was added. A reflux condenser was attached, and the flask was heated to 80° C. overnight. In the morning, the mixture was diluted with DCM and concentrated. The residue was taken up in 2-PrOH, heated briefly to boiling, then sonicated for 20 s. The mixture was cooled then filtered. The collected solid was washed with 2-PrOH, then dried under a stream of N2 (g). The filtration was repeated with the filtrate. The two lots of material were combined to give 5-(6-(benzylthio)-2-oxoquinolin-1(2H)-yl)-2-bromo-4-methoxybenzonitrile (798 mg, 1.672 mmol, 91% yield) as a light-orange solid. m/z (ESI) 477.0 (M+H)+.

Workup

  1. customto give a thick, yellow suspension
  2. customA reflux condenser was attached
  3. concentrationconcentrated
  4. temperatureheated briefly
  5. customsonicated for 20 s
  6. temperatureThe mixture was cooled
  7. filtrationthen filtered
  8. washThe collected solid was washed with 2-PrOH
  9. dry with materialdried under a stream of N2 (g)
  10. filtrationThe filtration

Sources & evidence

ORD record
ord-31e8fe03d45148239cb90a05e9c032ea
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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