Ethylamine → 5-Ethylcarbamoyl-4'-methyl-biphenyl-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9](I)[CH:10]=1)=[O:4].[CH2:19]([NH2:21])[CH3:20].C1CCN2C(=NCCC2)CC1.C1C[O:36][CH2:35]C1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([C:35](=[O:36])[NH:21][CH2:19][CH3:20])[CH:10]=1)=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A 20 mL of vial was charged with 5-iodo-4′-methyl-biphenyl-3-carboxylic acid methyl ester (500 mg, 1.42 mmol), Pd(OAc)2 (9.6 mg, 0.043 mmol), Mo(CO)6 (413.5 mg, 1.566 mmol), ethylamine (2.0 M in MeOH, 1.068 mL, 2.136 mmol), DBU (426 uL, 2.848 mmol) and dry THF (10 mL). The vial was immediately capped with a Teflon septum under air and irradiated with microwaves to 100° C. for 15 minutes. After cooling, the reaction mixture was filtered through a short celite pad and the solvent, and excess DBU was removed under reduced pressure. The residue was purified by preparative HPLC to afford 210 mg of 5-ethylcarbamoyl-4′-methyl-biphenyl-3-carboxylic acid methyl ester (yield 50%). MS (M+H)=298.
Workup
- customirradiated with microwaves to 100° C. for 15 minutes
- temperatureAfter cooling
- filtrationthe reaction mixture was filtered through a short celite pad
- customthe solvent, and excess DBU was removed under reduced pressure
- customThe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-13799069e3f741cb8cec0032d1773a0c
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193368B2
Reaction notes
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