(1-Methoxy-2-phenylvinyloxy)trimethylsilane → methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate

HRID 563428Notes

Reaction equation

HRID 563428 reaction equation
C(O[CH:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][N:16]=[CH:15]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[CH3:21][O:22][C:23]([O:31][Si](C)(C)C)=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[NH:17]1[C:18]2[C:14](=[CH:13][C:12]([CH:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:23]([O:22][CH3:21])=[O:31])=[CH:20][CH:19]=2)[CH:15]=[N:16]1

Participants

5

Reactant 2

HCID 54141957(1-Methoxy-2-phenylvinyloxy)trimethylsilaneHCID 67005800(1H-indazol-5-yl)(phenyl)methyl acetate

Product 1

HCID 59252820methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoateYield 60%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-indazol-5-yl)(phenyl)methyl acetate (245 mg, 0.8 mmol) and (1-methoxy-2-phenylvinyloxy)trimethylsilane (1.78 g, 8.0 mmol, prepared using General Silyl Ketene Acetal Method A) in 20 mL of dry DCM was added TiCl4 (0.8 mL of 1.0 M DCM solution, 0.8 mmol) and then stirred 3 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated. MPLC purification using a 0-40% EtOAc/hexane gradient gave 170 mg (60% yield) of methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate. MS found: (M+H)+=357.

Workup

  1. customThe reaction was quenched with MeOH
  2. additionpoured into aqueous sodium bicarbonate
  3. extractionextracted 2×EtOAc
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customMPLC purification

Sources & evidence

ORD record
ord-859385e2844f4ceab5b1f8966f05a8fa
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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