Benzoic Acid → (1,1'-Biphenyl)-2-carboxamide
Reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C1C=CC=CC=1.C[N:23]([C:25]([O:29]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C[C@@H]1CC[C@H](C2C=CC=CC=2)N1>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6]([C:25]([NH2:23])=[O:29])=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Biphenyl acid 10 (40 mg, 0.064 mmol, 1 eq) and HBTU (49 mg, 0.13 mmol, 2 eq) were dissolved in DMF (1 mL) followed by the addition of N,N-dimethyl-1-((2S,5R)-5-phenylpyrrolidin-2-yl)methanamine 250 (23 mg, 0.13 mmol, 2 eq). The reaction mixture was stirred for 2 h, diluted with EtOAc and quenched with a saturated aqueous NaHCO3 solution. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford an oil. The crude oil was purified by silica gel chromatography (2-5% MeOH/DCM, 0.1% Et3N) to afford 23 mg of biphenyl amide 247. Yield 45%.
Workup
- customquenched with a saturated aqueous NaHCO3 solution
- extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
- dry with materialthe combined organics were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto afford an oil
- customThe crude oil was purified by silica gel chromatography (2-5% MeOH/DCM, 0.1% Et3N)
Sources & evidence
- ORD record
- ord-0ccfe11a66ca47309102a7ea433f10e7
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928244B2
Reaction notes
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