HCID 118324082, compound → (4-Chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol

HRID 1778308Notes

Reaction equation

HRID 1778308 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[N:15]=[CH:16][S:17][CH:18]=3)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][CH:3]=[C:2]3[Cl:1])([C:14]2[N:15]=[CH:16][S:17][CH:18]=2)[OH:13])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 118324082HCID 118324082, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 118324081(4-Chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-chloroquinolin-6-yl)(thiazol-4-yl)methanone (52 mg, 0.189 mmol) in THF (2 mL) was slowly added (4-chlorophenyl)magnesium bromide (0.246 mL, 0.246 mmol, 1M in THF) and the resulting solution was kept at 0° C. for 2 hr. The reaction was quenched with saturated NH4Cl at 0° C. and the aqueous mixture was extracted with EtOAc twice. The combined organics were concentrated and purified by silica column (40% EtOAc/hexanes) chromatography to yield (4-chlorophenyl)(4-chloroquinolin-6-yl)(thiazol-4-yl)methanol. (ES, m/z) [M+H]+ 387, 389.

Workup

  1. customThe reaction was quenched with saturated NH4Cl at 0° C.
  2. extractionthe aqueous mixture was extracted with EtOAc twice
  3. concentrationThe combined organics were concentrated
  4. custompurified by silica column (40% EtOAc/hexanes) chromatography

Sources & evidence

ORD record
ord-b3fd3ab4b73241448a577934773b77d0
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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