Ethyl Acetate → HCID 86760763, compound

HRID 271518Notes

Reaction equation

HRID 271518 reaction equation
Br[C:2]1[CH:6]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:4][C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1.[C:22](=[O:25])([O-])[O-].[Na+].[Na+].C(O[CH2:32][CH3:33])(=O)C>C1(C)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][O:25][N:8]=[C:7]1[C:32]2[C:33](=[CH:2][C:3]([C:2]3[CH:6]=[C:5]([CH2:7][N:8]4[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[O:4][C:3]=3[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=3)=[CH:14][CH:19]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 69312905HCID 69312905, compound

Product 1

HCID 86760763HCID 86760763, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of the products from Step 2 (0.6 g, 1.62 mmol) and Description 1 Step 2 (0.367 g, 1.8 mmol) in toluene (10 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (0.113 g, 0.162 mmol) and 2M aqueous sodium carbonate (0.2 ml, 3.93 mmol) and heated under reflux for 18 hours. After cooling to room temperature, the mixture was poured into ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, dried and reduced in vacuo. The crude title compound (0.310 g) was used in the next step without further purification; MS(ES+) m/e 449 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. customdried
  5. customThe crude title compound (0.310 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-b16da91523734796a0b2e584e6a263ee
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

Loading…