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

HRID 722187Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[ClH:20].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[CH:23]([CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=1)=[O:31])[CH2:22]2>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[ClH:20].[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:36]2[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[CH2:29][CH:23]3[CH:24]4[CH2:25][CH2:26][N:21]([CH2:28][CH2:27]4)[CH2:22]3)=[CH:38][CH:37]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

43.8 mg (0.24 mmol) of 3-(acetamido)phenylboronic acid, 0.33 ml (0.66 mmol) of 2M aqueous sodium carbonate solution and 8.1 mg (0.01 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride are added to a solution of 80 mg (0.22 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride in 1.5 ml of DMF. The reaction mixture is stirred at 80° C. for 0.14 h, cooled, filtered through kieselguhr and then purified by preparative HPLC. The product fractions are concentrated, taken up in methanol, mixed with 4M HCl in dioxane and again concentrated. Drying under high vacuum results in 23 mg (20% of theory) of the title compound.

Workup

temperaturecooled
filtrationfiltered through kieselguhr
custompurified by preparative HPLC
concentrationThe product fractions are concentrated
additionmixed with 4M HCl in dioxane
concentrationagain concentrated
customDrying under high vacuum

Sources & evidence

ORD record: ord-a6f60b2052a14ef5a9001db55abf9616
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138410B2

Reaction notes

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