Triethylamine → HCID 66808413, compound

HRID 2197794Notes

Reaction equation

HRID 2197794 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([S:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=[C:2]([NH2:1])[CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 66808413HCID 66808413, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 4c (0.500 g, 1.91 mmol) was dissolved in CH2Cl2 along with phenyl boronic acid (0.701 g, 5.74 mmol), copper(II) acetate (0.659 g, 3.83 mmol), and triethylamine (0.387 g, 3.83 mmol). Stirred at room temperature for 48 h, at which time 2 more equivalents of each reagent was added. Stirred at room temperature for another 16 h at which time another 2 eq of each reagent was added. Stirred at room temperature for another 16 h. The reaction was diluted with water and extracted with ethyl acetate Dried over Na2SO4, filtered and concentrated under vacuum giving the crude product which was purified silica gel column chromatography eluting with 20% EtOAc/hexane (0.100 g, 15%). The product was reduced with SnCl2 following the procedure from Example 1f to give the title compound (90 mg, 98%).

Workup

  1. additionwas added
  2. additionwas added
  3. stirringStirred at room temperature for another 16 h
  4. extractionextracted with ethyl acetate
  5. dry with materialDried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude product which
  9. customwas purified silica gel column chromatography
  10. washeluting with 20% EtOAc/hexane (0.100 g, 15%)

Sources & evidence

ORD record
ord-9dd40dcbcee343feab4a3ff0ec5ce3f5
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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