Triethylamine → Methyl 2-cyano-4-biphenylcarboxylate

HRID 1421772Notes

Reaction equation

HRID 1421772 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([C:18]#[N:19])[CH:5]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:18]#[N:19])[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:8][CH:9]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 53821226Methyl 3-Cyano-4-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 53846446Methyl 2-cyano-4-biphenylcarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-Cyano-4-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester from step 1 (2.5 g, 8.1 mmol) and phenylboronic acid (2 g, 16.2 mmol) were dissolved in DMF (33 ml) and treated with Et3N (3.1 ml, 17.8 mmol). Argon was bubbled into the solution for 20 min. and then a catalytic amount of PdCl2 (PPh3)2 (285 mg, 0.405 mmol) was added. The reaction mixture was warmed to 90° C. and stirred for 3 hours under argon atmosphere. The reaction was quenched with satd. NaHCO3 (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (10% EtOAc/Hexane) to yield the desired product.

Workup

  1. customArgon was bubbled into the solution for 20 min.
  2. customThe reaction was quenched with satd
  3. extractionNaHCO3 (20 mL) and extracted with EtOAc (2×20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ec050cd7113b42ac94b5bac477453797
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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