Ethyl 2-(4-amino-2-chloro-5-ethynylphenoxy)-4-fluorobenzoate → Ethyl 2-(6-chloro-1h-indol-5-yloxy)-4-fluorobenzoate

HRID 1043118Notes

Reaction equation

HRID 1043118 reaction equation
[NH2:1][C:2]1[C:20]([C:21]#[CH:22])=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:23])[CH:3]=1>C(O)C.C(OCC)(=O)C>[Cl:23][C:4]1[CH:3]=[C:2]2[C:20]([CH:21]=[CH:22][NH:1]2)=[CH:19][C:5]=1[O:6][C:7]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 87316240Ethyl 2-(4-amino-2-chloro-5-ethynylphenoxy)-4-fluorobenzoate

Product 1

HCID 67227741Ethyl 2-(6-chloro-1h-indol-5-yloxy)-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 242D (1.0 g) in ethanol (20 mL) was added NaAuCl4.2H2O (60 mg). The mixture was stirred at room temperature for 4 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated and the residue was loaded on a column and eluted with 10% ethyl acetate in hexane to give the pure product.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated
  5. washeluted with 10% ethyl acetate in hexane
  6. customto give the pure product

Sources & evidence

ORD record
ord-c750a3d6ecd840109c0be5ca3d720627
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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