Dimethylformamide → Ethyl 3'-amino-[1,1'-biphenyl]-3-carboxylate

HRID 1374261Notes

Reaction equation

HRID 1374261 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.C[N:35](C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:35][C:13]1[CH:14]=[C:15]([C:2]2[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 143542Ethyl 3-iodobenzoate

Product 1

HCID 11975548Ethyl 3'-amino-[1,1'-biphenyl]-3-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
80 °C

Procedure

Preparation H3, Step 1: Ethyl 3-iodobenzoate (0.92 g, 3.34 mmol, 1 eq.), phenylboronic acid (0.87 g, 5.02 mmol, 1.5 eq.), palladium(II)acetate (37 mg, 0.167 mmol, 0.05 eq.) and sodium carbonate (706 mg, 6.66 mmol, 2 eq.) were dissolved in DMF (20 mL) at room temperature under nitrogen. The reaction was then heated at 80° C. for 1.5 hours. Worked up by adding ethyl acetate and rinsing 4 times with water. The organic layer was dried over sodium sulfate and stripped to give a dark oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to obtain 3′-Amino-[1,1′-biphenyl]-3-carboxylic acid, ethyl ester (420 mg) as an oil. Yield=55%. LCMS detects (M+H)+=242.41.

Workup

  1. customPreparation H3, Step 1
  2. washrinsing 4 times with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customto give a dark oil
  5. customPurified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7768b81f116745498de24cfadb6f2cc3
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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