Toluene → 6-Chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77714

Reaction equation

HRID 77714 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)O1.[Cl:19][C:20]1[CH:38]=[CH:37][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:25])=[CH:22][C:21]=1I.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.C(O)C>[Cl:19][C:20]1[C:21]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:22][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=2)=[O:25])=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 112651643-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzeneHCID 690440504-chloro-3-iodo-N-[3-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 692724446-Chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamideYield 146.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (0.40 g, 0.0016 mol) was mixed with 4-chloro-3-iodo-N-[3-(trifluoromethyl)phenyl]benzamide (0.600 g, 0.00141 mol), potassium carbonate (0.39 g, 0.0028 mol), toluene (10 mL), ethanol (1.7 mL), and water (1.1 mL). The mixture was degassed by bubbling nitrogen through it. To the reaction was added tetrakis(triphenyl-phosphine)palladium(0) (0.078 g, 0.000068 mol). The reaction was heated to reflux for 16 hours. LCMS showed about 80% conversion to M+H 421/423 (3:1). The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, then dried (Na2SO4). Solvent was removed under vacuum to give 0.87 g oil. The product was purified by automatic flash chromatography on silica gel. Used a 40 g column; flow 40 mL/min; [A=hexane] [B=EtOAc]. A, 4 min; Gradient to 20% B in 30 min. The product eluted in 23-28 min (starting material at 16-18 min). Removal of solvent under vacuum gave 0.46 g white solid.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through it
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 16 hours
  5. extractionThe reaction was extracted with ethyl acetate
  6. washthe organic extracts were washed with water, saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-e381516e07d94b3dace2255546566371
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Linked notes

Loading…