Triethylamine → HCID 66808413, compound

HRID 2358629Notes

Reaction equation

HRID 2358629 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-7484036d799743aa83f9fa76ada9d1fa
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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