Trifluoroacetic acid → HCID 58046306, compound

HRID 2359327Notes

Reaction equation

HRID 2359327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](O)[C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][C:11]=2[O:19][CH3:20])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][C:11]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 58046323HCID 58046323, compound

Product 1

HCID 58046306HCID 58046306, compoundYield 122.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((3,4-dichlorophenyl)(hydroxy)methyl)-3-methoxybenzamide (Preparation 156, 142 mg, 0.435 mmol) in DCM (5 mL) was added TFA (0.065 mL, 0.870 mmol) followed by triethylsilane (0.083 mL, 0.522 mmol) and the reaction stirred at room temperature for 72 hours. Further TFA (0.065 mL, 0.870 mmol) and triethylsilane (0.083 mL, 0.522 mmol) were added and the reaction stirred for a further 24 hours. The reaction was partitioned between saturated aq. NH4Cl (20 mL), and EtOAc (20 mL). The layers were separated and the aqueous was extracted with EtOAc (2×20 mL). The combined organics were washed with brine (20 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a white solid (165 mg, 100%). The material was used as crude in the next reaction without further purification.

Workup

  1. stirringthe reaction stirred for a further 24 hours
  2. customThe reaction was partitioned between saturated aq. NH4Cl (20 mL), and EtOAc (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-05cfc48be1094d949e119e3cf28f2f6e
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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