Triethylamine → HCID 86586377, compound

HRID 431379Notes

Reaction equation

HRID 431379 reaction equation
[N+](C1[CH:5]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH:7]=[C:8]([N+:10]([O-])=O)C=1)([O-])=O.B(O)[OH:25].[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.[Cl:34][C:35]1[CH:36]=C(C=[C:42]([Cl:44])[CH:43]=1)C(Cl)=O>C(Cl)Cl.[Pd]>[NH2:10][C:8]1[CH:31]=[C:30]([N:29]([C:32]2[CH:33]=[C:42]([Cl:44])[CH:43]=[C:35]([Cl:34])[CH:36]=2)[CH:27]=[O:25])[CH:5]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 61668Boronic AcidHCID 761913,5-Dichlorobenzoyl chlorideHCID 86586378HCID 86586378, compound

Product 1

HCID 86586377HCID 86586377, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (3,5-dinitrophenyl)[3-(trifluoromethyl) phenyl]amine, prepared as previously described via boronic acid coupling (0.50 g, 1.5 mmol) in CH2Cl2 (7 mL) was treated with 10% palladium/carbon (100 mg) and the mixture shaken 1 h. under 50 psi H2. The solution was filtered and the filtrate treated with triethylamine (0.15 g, 1.5 mmol) followed by 3,5-dichlorobenzoyl chloride (0.29 g, 1.4 mmol) and stirred overnight. The reaction mixture was then concentrated and the product purified on silica gel using 2:1 hexane:ethyl acetate as eluent to give 0.54 g (80%) of the desired product as a white solid: 1H NMR 400 MHz (DMSO) δ5.17 (s, 2H); 6.16 (s, 1H); 6.69 (s, 1H); 6.82 (s, 1H); 7.05 (t, J=8 Hz, 1H); 7.26-7.44 (m, 4H); 7.94 (s, 2H); 8.30 (s, 1H); 10.08 (s, 1H);

Workup

  1. filtrationThe solution was filtered
  2. stirringstirred overnight
  3. concentrationThe reaction mixture was then concentrated
  4. customthe product purified on silica gel using 2:1 hexane

Sources & evidence

ORD record
ord-d7e768e7de404b33b8475df57917243c
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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