Cesium carbonate → N-[4-(2-Thienyl)phenyl]-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

HRID 722177Notes

Reaction equation

HRID 722177 reaction equation
[ClH:1].Br[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[ClH:1].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27339602-Thiopheneboronic acidHCID 21883433N-(4-Bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

Product 1

HCID 10236954N-[4-(2-Thienyl)phenyl]-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

90 mg (0.26 mmol) of N-(4-bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide hydrochloride, 40 mg (0.31 mmol) of 2-thiopheneboronic acid, 190 mg (0.57 mmol) of cesium carbonate and 20 mg (0.03 mmol) of bis(diphenylphosphino)ferrocenepalladium(II) chloride are reacted in 1 ml of 1,2-dimethoxyethane by the general method. 14.1 mg (15% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-207186f9262343d8a7aaffad667645e1
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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