Cesium carbonate → N-[4'-(Hydroxymethyl)-1,1'-biphenyl-4-yl]-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

HRID 722178Notes

Reaction equation

HRID 722178 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.[OH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[ClH:1].[OH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]3[CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)=[O:11])=[CH:5][CH:4]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 21883433N-(4-Bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Hydrochloride

Product 1

HCID 21883439N-[4'-(Hydroxymethyl)-1,1'-biphenyl-4-yl]-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, 50 mg (0.31 mmol) of 4-(hydroxymethyl)phenylboronic 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. 5.9 mg (6% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-128ec2588352439cb8d6533cc5653def
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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