3-Nitrophenylboronic Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(3'-nitro-1,1'-biphenyl-4-yl)acetamide Hydrochloride

HRID 722184Notes

Reaction equation

HRID 722184 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[ClH:19].[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[CH:22]([CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=1)=[O:30])[CH2:21]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:19].[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[CH:22]([CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[CH:34][CH:33]=1)=[O:30])[CH2:21]2

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 218834482-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide Hydrochloride

Product 1

HCID 218834552-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(3'-nitro-1,1'-biphenyl-4-yl)acetamide Hydrochloride

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

61.3 mg (0.37 mmol) of 3-nitrophenylboronic acid, 0.5 ml (1.0 mmol) of 2M aqueous sodium carbonate solution and 12.2 mg (0.02 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride are added to a solution of 120 mg (0.33 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride in 2 ml of DMF. The reaction mixture is stirred at 80° C. for 14 h, cooled, filtered through kieselguhr and then purified by preparative HPLC. The product fractions are concentrated, taken up in a 5:1 mixture of methanol and 1M hydrochloric acid and again concentrated. Drying under high vacuum results in 13 mg (9.7% of theory) of the title compound.

Workup

  1. temperaturecooled
  2. filtrationfiltered through kieselguhr
  3. custompurified by preparative HPLC
  4. concentrationThe product fractions are concentrated
  5. additiontaken up in a 5:1 mixture of methanol and 1M hydrochloric acid
  6. concentrationagain concentrated
  7. customDrying under high vacuum

Sources & evidence

ORD record
ord-054ed61a48b1420fb6f57869fc0a35ad
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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