HCID 118324051, compound → HCID 118324147, compound

HRID 1778293Notes

Reaction equation

HRID 1778293 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][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]=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118324051HCID 118324051, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118324147HCID 118324147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromoquinolin-6-yl)(4-chlorophenyl)methanone (0.25 g, 0.72 mmol) in THF (5 mL) was slowly added (4-chlorophenyl)magnesium bromide (1.08 mL, 1 M in THF) at 0° C. under the argon. The resulting solution was kept at 0° C. for 3 hr. The reaction was quenched with saturated NH4Cl at 0° C. and the aqueous mixture was extracted with EtOAc 2 times. The combined organics were concentrated and purified by silica column chromatography (20-30% EtOAc/hexanes) to yield (4-bromoquinolin-6-yl)bis(4-chlorophenyl)methanol. (M+H)+: 458, 460.

Workup

  1. customat 0° C.
  2. customThe reaction was quenched with saturated NH4Cl at 0° C.
  3. extractionthe aqueous mixture was extracted with EtOAc 2 times
  4. concentrationThe combined organics were concentrated
  5. custompurified by silica column chromatography (20-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2aa17aa9303c4a2baa2563b7c393ea33
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…