Triethylamine → HCID 59820941, compound

HRID 1363654Notes

Reaction equation

HRID 1363654 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:19]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343204-tert-Butylphenylboronic acidHCID 27607274'-Trifluoromethoxy-biphenyl-4-ylamine

Product 1

HCID 59820941HCID 59820941, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 4-amino-4′-(trifluoromethoxy)biphenyl (compound of Example 3(2); 112 mg, 0.442 mmol), 4-(tert-butyl)phenylboronic acid (87 mg, 0.486 mmol), copper(II) acetate (40 mg, 0.221 mmol), triethylamine (0.061 ml, 0.884 mmol) and pyridine (3.0 ml) was stirred at 50° for 2 hours. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was diluted with 1N hydrochloric acid (10 ml), and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (50 mg, 29%) as a pale yellow solid.

Workup

  1. filtrationfiltered through celite
  2. additionThe filtrate was diluted with 1N hydrochloric acid (10 ml)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b90f3f2f2d564ae3bc742cbd8cfdf414
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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