Water → HCID 87212268, compound

HRID 2280581Notes

Reaction equation

HRID 2280581 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7](OC)[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([O:19][CH3:20])[CH:4]=1)=[O:2].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:30](=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[CH:8]=[CH:7][C:6]=1[C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH3:30])[CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 11045242HCID 11045242, compound

Product 1

HCID 87212268HCID 87212268, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The triflate 3 was dissolved in toluene followed by the addition of phenyl boronic acid, tetrakis(triphenylphosphine)Pd, potassium carbonate and water in a microwave tube equipped with a stir bar. The tube was sealed and the reaction was carried out in a microwave synthesizer for 15 mins at 120° C. and 100 watts. After the completion of the reaction the reaction mixture was dissolved in DCM washed with sodium bicarbonate, water and brine. The product was isolated as clear viscous oil using 10% EtOAc/hexanes as the solvent system. Yield=73.0% (Rf=0.27; 10% EtOAc/hexanes), 1H NMR, 500 MHz Varian, CDCl3, δ 10.01 (s, 1H), 7.53 (d, J=15.00 Hz, 1H), 7.51 (d, J=15.00 Hz, 1H), 7.49 (d, J=10.00 Hz, 1H), 7.34 (s, 3H), 7.21 (d, J=7.0, 1H), 3.89 (s, 3H), 2.41 s, 3H), MS: m/z (ESI, pos.)=249.2 ([M+23])

Workup

  1. customequipped with a stir bar
  2. customThe tube was sealed
  3. customAfter the completion of the reaction the reaction mixture
  4. washwashed with sodium bicarbonate, water and brine
  5. customThe product was isolated as clear viscous oil

Sources & evidence

ORD record
ord-e15f4d58b54f4ccbbc2be77b9ea2beb1
Source dataset
uspto-grants-2015_09
Patent number
US09139546B2

Reaction notes

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