Ethanol → HCID 23599443, compound

HRID 1350908Notes

Reaction equation

HRID 1350908 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[NH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([NH2:18])[CH:24]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 952706HCID 952706, compound

Product 1

HCID 23599443HCID 23599443, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared by a method analogous to that described in Example 1 from (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(5-bromofuran-2-carboxamide) and 3-aminophenylboronic acid, using tetrakis(triphenylphosphine)palladium (0) and sodium carbonate in a mixture of tetrahydrofuran, ethanol and water. The compound was purified by flash chromatography using 5–20% 3.5M methanolic ammonia/chloroform mixtures as the eluent and then by reverse phase HPLC on a Waters Bondapak® C18 column using a gradient of acetonitrile and 0.1% aqueous trifluoroacetic acid as the eluent. The free base was prepared by basification of the product-containing fractions and extraction into chloroform followed by evaporation to gave the title compound; MS (ES+) 312 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customThe compound was purified by flash chromatography
  3. customThe free base was prepared by basification of the product-containing fractions and extraction into chloroform
  4. customfollowed by evaporation

Sources & evidence

ORD record
ord-71b4e3ab0f044808a1578397ca79bd66
Source dataset
uspto-grants-2007_05
Patent number
US07214688B2

Reaction notes

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