Sodium Carbonate → HCID 57531253, compound

HRID 1454994Notes

Reaction equation

HRID 1454994 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]([NH:23][CH3:24])=[O:22])=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>C1(C)C=CC=CC=1.C(O)C>[Cl:31][C:32]1[CH:37]=[C:36]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]([NH:23][CH3:24])=[O:22])=[O:18])[CH2:13][CH2:12]3)[CH:3]=2)[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 67307138HCID 67307138, compound

Product 1

HCID 57531253HCID 57531253, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 0.14 g (0.35 mmol) of 2-(methylamino)-2-oxoethyl 4-[3-(3-bromophenyl)propyl]piperazine-1-carboxylate, prepared in step 7.2., in a mixture of 4 ml of toluene and 0.6 ml of ethanol is admixed with 0.08 g (0.07 mol) of the tetrakis(triphenylphosphine)palladium complex, 1.05 ml (2.1 mmol) of a 2M aqueous solution of sodium carbonate and 0.22 g (1.4 mmol) of 3-chlorobenzeneboronic acid. The mixture is heated to 150° C. under microwave irradiation for 5 minutes and the organic phase is recovered by filtration on a cartridge equipped with a frit and containing celite and sodium sulphate. The cartridge is rinsed with toluene and the filtrate is concentrated under reduced pressure. The product is purified by chromatography on silica gel, eluting with a 90/10 mixture of ethyl acetate and methanol. The eluate is subsequently taken up in n-heptane, to give 0.086 g (0.18 mmol) of product in the form of white crystals.

Workup

  1. customprepared in step 7.2
  2. filtrationthe organic phase is recovered by filtration on a cartridge
  3. customequipped with a frit
  4. additioncontaining celite and sodium sulphate
  5. washThe cartridge is rinsed with toluene
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe product is purified by chromatography on silica gel
  8. washeluting with a 90/10 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-66bd7e2e7f294085bcf60044906c52ca
Source dataset
uspto-grants-2009_01
Patent number
US07482346B2

Reaction notes

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