Lithium acetate → HCID 67457614, compound

HRID 1922159Notes

Reaction equation

HRID 1922159 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]([CH3:14])[CH3:13])[C:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=1)=[C:7]2[CH3:27].C([Si]([O:43][C:44]([O:46][CH3:47])=[CH2:45])(C)C)(C)(C)C.C([O-])(=O)C.[Li+]>O1CCCC1>[CH3:47][O:46][C:44](=[O:43])[CH2:45][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:27])=[C:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=1)[C:9]([CH:12]([CH3:13])[CH3:14])=[N:10]2

Participants

5

Reactant 3

HCID 3474584Lithium acetateHCID 45644911-(tert-Butyldimethylsilyloxy)-1-methoxyetheneHCID 86642382HCID 86642382, compound

Product 1

HCID 67457614HCID 67457614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trifluoromethanesulfonic acid 8-chloro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yl ester (0.075 g), tert-butyl-(1-methoxyvinyloxy)dimethylsilane (0.063 mL), lithium acetate (0.029 g) and tetrahydrofuran (2.0 mL) was purged with argon for 30 minutes, and then treated with tetrakis(triphenylphosphine)palladium (0) (0.017 g). The mixture was stirred at 70° C. for four days, cooled to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (10:0 to 2:8 by volume) to give title compound as pale yellow oil (0.042 g).

Workup

  1. customwas purged with argon for 30 minutes
  2. additiontreated with tetrakis(triphenylphosphine)palladium (0) (0.017 g)
  3. temperaturecooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (10:0 to 2:8 by volume)

Sources & evidence

ORD record
ord-df6a147bcf894177bee2e5cceabdabc3
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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