HCID 178418573, compound → HCID 178462274, compound

HRID 2391017Notes

Reaction equation

HRID 2391017 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH:13]=[O:14])[CH2:9][CH2:8]1)=[O:5].[CH3:23][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:14])[CH3:23])[CH2:9][CH2:8]1)=[O:5]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178520978HCID 178520978, compound

Product 1

HCID 178462274HCID 178462274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of trans-2-chloro-N-(4-formylcyclohexyl)-5-(trifluoromethyl)-benzamide (1.00 g, 3.00 mmol) in THF (50 mL) is added methylmagnesium bromide 2.5 mL of a 3M solution in THF, 7.49 mmol,) and the reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with water and partitioned between EtOAc and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo. The mixture is used directly in step 2 without further purification.

Workup

  1. customThe reaction mixture is quenched with water
  2. custompartitioned between EtOAc and water
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe mixture is used directly in step 2 without further purification

Sources & evidence

ORD record
ord-eb181c086eef4bcebffdd11b32107003
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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