Sodium Carbonate → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1-benzofuran-2-carboxamide hydrochloride

HRID 2179641Notes

Reaction equation

HRID 2179641 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[ClH:37].[N:38]12[CH2:45][CH2:44][CH:41]([CH2:42][CH2:43]1)[C@@H:40]([NH:46][C:47]([C:49]1[O:50][C:51]3[C:57](Br)=[CH:56][CH:55]=[CH:54][C:52]=3[CH:53]=1)=[O:48])[CH2:39]2.C(=O)([O-])[O-].[Na+].[Na+]>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:37].[N:38]12[CH2:43][CH2:42][CH:41]([CH2:44][CH2:45]1)[C@@H:40]([NH:46][C:47]([C:49]1[O:50][C:51]3[C:57]([C:2]4[CH:7]=[CH:6][C:5]([N:8]5[CH2:12][CH2:11][CH2:10][C:9]5=[O:13])=[CH:4][CH:3]=4)=[CH:56][CH:55]=[CH:54][C:52]=3[CH:53]=1)=[O:48])[CH2:39]2

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 7361101-(4-Bromophenyl)pyrrolidin-2-oneHCID 2733548Bis(pinacolato)diboraneHCID 67313982N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride

Product 1

HCID 67314562N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1-benzofuran-2-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Procedure

161.9 mg (0.67 mmol) of 1-(4-bromophenyl)-2-pyrrolidinone, 197.5 mg (0.78 mmol) of bis(pinacolato)diboron, 165.4 mg (1.69 mmol) of potassium acetate, 19.0 mg (0.03 mmol) of PdCl2(dppf), 200 mg (0.52 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride (Example 30A), 1.30 ml of 2 M sodium carbonate solution and a further 19.0 mg (0.03 mmol) of PdCl2(dppf) in 2.5 ml of DMF are reacted by general method D. Drying under high vacuum results in 166.6 mg (65% of theory) of the title compound.

Workup

  1. customDrying under high vacuum

Sources & evidence

ORD record
ord-12d863d9599a41f5830592f284487384
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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