Triethylsilane → HCID 118324012, compound

HRID 1778302Notes

Reaction equation

HRID 1778302 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][CH:20]=[C:19]3/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)O)=[CH:5][CH:4]=1.C([SiH](CC)CC)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][CH:20]=[C:19]3/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 118324106HCID 118324106, compound

Product 1

HCID 118324012HCID 118324012, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-(4-methoxyphenyl)(4-styrylquinolin-6-yl)(thiazol-2-yl)methanol (33 mg, 0.0732 mmol) and triethylsilane (0.035 mL, 0.22 mmol) in CH2Cl2 (2 mL) at −78° C. was added dropwise TiCl4 (0.22 mL, 0.22 mmol). The resulting mixture (turned to dark green suspension) was kept at −78° C. for 20 min and then warmed to 0° C. The reaction was maintained at 0° C. for 1 hr and then quenched with ice, CH2Cl2 and aqueous NaOH until the aqueous layer became basic. The aqueous layer was extracted with CH2Cl2 twice. The combined organics were concentrated and purified by chromatography (silica column, 25% EtOAc/CH2Cl2) to yield (E)-2-((4-methoxyphenyl)(4-styrylquinolin-6-yl)methyl)thiazole.

Workup

  1. temperatureThe reaction was maintained at 0° C. for 1 hr
  2. customquenched with ice, CH2Cl2 and aqueous NaOH until the aqueous layer
  3. extractionThe aqueous layer was extracted with CH2Cl2 twice
  4. concentrationThe combined organics were concentrated
  5. custompurified by chromatography (silica column, 25% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-34efacc28d374c9ebc5ae16632169d23
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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