(1-Methoxy-2-phenylvinyloxy)trimethylsilane → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoate

HRID 218149Notes

Reaction equation

HRID 218149 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]([O:35][Si](C)(C)C)=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27]([O:26][CH3:25])=[O:35])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 54141957(1-Methoxy-2-phenylvinyloxy)trimethylsilaneHCID 59251034HCID 59251034, compound

Product 1

HCID 68705735methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoateYield 84%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (318 mg, 1.0 mmol) and (1-methoxy-2-phenylvinyloxy)trimethylsilane (3 mmol) which was prepared using General Silyl Ketene Acetal Method A in 10 mL of dry DCM was added TiCl4 (1.0 mL of 1.0 M DCM solution, 1.0 mmol) and then stirred 1 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2× EtOAc. The organic layers were dried over MgSO4, filtered, concentrated and purified on SiO2 by MPLC using a EtOAc/hexane gradient to give 376 mg (84% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoate. MS found: (M+H)+=451.

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. custompurified on SiO2 by MPLC

Sources & evidence

ORD record
ord-93b7c4336048443fa92bcde9edb33a08
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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