Bromobenzene → HCID 11260802, compound

HRID 1831775Notes

Reaction equation

HRID 1831775 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:16].Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CC(C)([O-])C.[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:21][CH2:20]1)=[O:16]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 22052381HCID 22052381, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 11260802HCID 11260802, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 100 mg (0.2 mmol) 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-N-piperidin-4-ylmethyl-benzamide, 50 mg (0.32 mmol) Bromobenzene, 70 mg sodium-t-butoxide in 5 ml dioxane were purged with argon for 10 min. Then 37 mg of 2-(Dicyclohexylphosphino)biphenyl and 20 mg Pd2(dba)3 were added under argon and the mixture refluxed overnight. The residue was taken up in 3 ml saturated NaHCO3 solution and filtered through a chem elut® cartridge by elution with ethyl acetate. Subsequent removal of the solvent under reduced pressure and purification by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.5% TFA) the fractions containing the product were evaporated and lyophilised.

Workup

  1. customwere purged with argon for 10 min
  2. additionThen 37 mg of 2-(Dicyclohexylphosphino)biphenyl and 20 mg Pd2(dba)3 were added under argon
  3. temperaturethe mixture refluxed overnight
  4. filtrationfiltered through a chem elut® cartridge by elution with ethyl acetate
  5. customSubsequent removal of the solvent
  6. customunder reduced pressure and purification by preparative HPLC (
  7. washC18 reverse phase column, elution with a H2O/MeCN gradient with 0.5% TFA) the fractions
  8. additioncontaining the product
  9. customwere evaporated

Sources & evidence

ORD record
ord-4023ab0c96024718a3de9eb2e5b98304
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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