HCID 118324136, compound → HCID 118324075, compound

HRID 1778256Notes

Reaction equation

HRID 1778256 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([Br:21])[CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:22][CH3:23])[CH:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>O1CCCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)([C:9]2[CH:10]=[C:11]3[C:6](=[C:7]([Br:21])[CH:8]=2)[N:5]=[C:4]([O:22][CH3:23])[CH:3]=[C:2]3[Br:1])[OH:13])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 118324136HCID 118324136, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118324075HCID 118324075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 4,8-dibromo-6-[(4-chlorophenyl)carbonyl]-2-methoxyquinoline (1.5 g, 3.29 mmol, 1.00 equip) in tetrahydrofuran (30 mL). To the resulting mixture was then added (4-chlorophenyl)magnesium bromide (9.87 mL, 3.00 equip, 1 M) dropwise with stirring at 0° C. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of saturated sodium bicarbonate (100 mL). The solids were filtered out and washed with ethyl acetate (100 mL), and the ethyl acetate was combined with the filtrate. The resulting solution was extracted with ethyl acetate (100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:9) to yield bis(4-chlorophenyl)(4,8-dibromo-2-methoxyquinolin-6-yl)methanol as a yellow solid. LCMS (ES, m/z) 568 [M+H]+

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of saturated sodium bicarbonate (100 mL)
  3. filtrationThe solids were filtered out
  4. washwashed with ethyl acetate (100 mL)
  5. extractionThe resulting solution was extracted with ethyl acetate (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solids were filtered out
  8. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0154716ba5bc456eb44e5838cc147c7a
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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