Allyl bromide → HCID 86651613, compound

HRID 472678Notes

Reaction equation

HRID 472678 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:39])[C:16]([N:18]2[CH2:23][CH2:22][C:21](=[N:24][S:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])[CH2:20][C@@H:19]2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[CH3:38])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:42](Br)[CH:43]=[CH2:44].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O.[Zn]>[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:39])[C:16]([N:18]2[CH2:23][CH2:22][C@@:21]([NH:24][S:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])([CH2:44][CH:43]=[CH2:42])[CH2:20][C@@H:19]2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[CH3:38])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 86651612HCID 86651612, compound2×

Product 1

HCID 86651613HCID 86651613, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of (2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-4-{[(1,1-dimethylethyl)sulfinyl]imino}-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide (Intermediate 1, 50 mg, 0.082 mmol) and Zinc powder (16.14 mg, 0.247 mmol, Aldrich) in THF (1.5 mL) was added at 25° C. allyl bromide (0.021 mL, 0.247 mmol, Aldrich) and the reaction mixture was stirred at this temperature for 16 hrs. Brine and EtOAc were added and the resulting mixture was filtrated over Celite® and the two phases were separated. The aqueous phase was extracted with EtOAc (3×) and the combined organic phases were dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography on silica with SP1 (Biotage) system (from 1:0 to 0:1 Cyclohexane/EtOAc; 25M Si cartridge) to give two different products:

Workup

  1. filtrationthe resulting mixture was filtrated over Celite®
  2. customthe two phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc (3×)
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography on silica with SP1 (Biotage) system (from 1:0 to 0:1 Cyclohexane/EtOAc; 25M Si cartridge)
  7. customto give two different products

Sources & evidence

ORD record
ord-af86b54ad2d94da6881160092dedb56a
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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