Triethylamine → HCID 23502780, compound

HRID 1835367Notes

Reaction equation

HRID 1835367 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.C(N(CC)CC)C.[SH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1.C(OCC)(=O)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([S:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[N:11][CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamideHCID 178418616HCID 178418616, compound

Product 1

HCID 23502780HCID 23502780, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg (0.432 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4), 0.090 ml (0.65 mmol) triethylamine and 59 mg (0.52 mmol) 2-mercaptopyridine in 4 ml tetrahydrofuran was deoxygenated by three freeze-thaw cycles. After addition of 15 mg (0.022 mmol) bis(triphenylphosphine)palladium(II) chloride the reaction mixture was heated at reflux over night. Cooling to room temperature was followed by dilution with ethyl acetate and washing with saturated aqueous sodium carbonate solution and brine. The combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate and concentrated. Column chromatography afforded 210 mg (87%) of the title compound as a light yellow amorphous mass.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. washwashing with saturated aqueous sodium carbonate solution and brine
  4. extractionThe combined aqueous layers were extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-10d18fede8d74cbc83f2ee1e76fcfc48
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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