Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → HCID 59252780, compound

HRID 563369Notes

Reaction equation

HRID 563369 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]([C:17]4(O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]([O:30][Si](C)(C)C)=[C:27]([CH3:29])[CH3:28]>ClCCCl.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]([C:17]4([C:27]([CH3:29])([CH3:28])[C:26]([O:25][CH3:24])=[O:30])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 59252751HCID 59252751, compound

Product 1

HCID 59252780HCID 59252780, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)cyclohexanol (500 mg, 1.6 mmol) in DCE (20 mL) was added 1-methoxy-2-methyl-1-trimethylsiloxy-propene (935 uL, 4.8 mmol) followed by TiCl4 (1.7 mL of 1.0 M in DCM). Within 10 min, the reaction was complete. The reaction was quenched with MeOH and then extracted from brine containing dilute HCl with EtOAc×4. The organic layers were dried over MgSO4, filtered, concentrated and purified on SiO2 using 25% EtOAc in hexanes to give 635 mg (100%) of methyl 2-(1-(1-(4-fluorophenyl)-1H-indazol-5-yl)cyclohexyl)-2-methylprop-anoate MS found: (M+H)+=395.

Workup

  1. customThe reaction was quenched with MeOH
  2. extractionextracted from brine containing dilute HCl with EtOAc×4
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on SiO2 using 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-23d546884dba48b78970d9f80d43e32b
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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