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

HRID 573099Notes

Reaction equation

HRID 573099 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-afac251dda974673b2eb57a36fa4fb3f
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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