Sodium Carbonate → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4'-methoxy-1,1'-biphenyl-4-yl)acetamide Hydrochloride

HRID 722182Notes

Reaction equation

HRID 722182 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)=[O:12])[CH2:3]2.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)=[CH:16][CH:15]=1)=[O:12])[CH2:3]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 218834482-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide Hydrochloride

Product 1

HCID 218834722-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4'-methoxy-1,1'-biphenyl-4-yl)acetamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In accordance with the general method, 60 mg. (0.17 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride, 25.4 mg (0.17 mmol) of 4-methoxyphenylboronic acid, 0.17 ml of 2M sodium carbonate solution and 6.1 mg (0.01 mmol) of bis(diphenylphosphino)ferrocenepalladium(II) chloride are reacted in 1 ml of dimethylformamide. 34 mg (50% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-cf96803926c449a2b0bf303d6a084ecc
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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