Ethanol → HCID 10221548, compound

HRID 891451Notes

Reaction equation

HRID 891451 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[S:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[Cl: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[S:13][C:14]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:18])[CH:24]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 9836523HCID 9836523, compound

Product 1

HCID 10221548HCID 10221548, 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-bromothiophene-2-carboxamide) and 3-chlorophenylboronic 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 a gradient of 5%-20% 3.5M methanolic ammonia/chloroform mixtures as the eluent to give the title compound as a colourless solid; MS (ES+) 347 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-f3bbc6f1c8354e599d45381d5229bcf8
Source dataset
uspto-grants-2006_02
Patent number
US07001914B2

Reaction notes

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