Sodium Carbonate → HCID 11300879, compound

HRID 969966Notes

Reaction equation

HRID 969966 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:12]3[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]3)[CH2:8]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[N+]1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:9]12[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10]1)[CH:7]([O:6][C:5]1[CH:15]=[CH:16][C:2]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:17])[CH:23]=3)=[CH:3][CH:4]=1)[CH2:8]2

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chlorideHCID 210726043-(4-Iodophenoxy)-1-azabicyclo[2.2.2]octane

Product 1

HCID 11300879HCID 11300879, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1A (330 mg, 1 mmol) in toluene (8 mL) was treated with 3-amino-phenylboronic acid (Lancaster, 276 mg, 2 mmol), Pd2(dba)3 (Strem Chemicals, 18.3 mg, 0.02 mmol), 1,3-bis(2,6-di-i-propylphenyl)imidazolium chloride, 95%, 26.9 mg, 0.06 mmol), and Na2CO3 (aqueous, 2M, 2 mL, 4 mmol) at 110° C. for 15 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (20 mL), and washed with brine (2×5 mL). The organic phase was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as oil (230 mg, yield, 78%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40-1.53 (m, 1H), 1.62-1.85 (m, 2H), 1.96-2.20 (m, 2H), 2.80-2.94 (m, 5H), 3.28-3.40 (m, 1H), 4.52-4.60 (m, 1H), 6.66 (ddd, J=7.8, 2.3, 1.0 Hz, 1H), 6.89 (ddd, J=7.3, 1.6, 1.0 Hz, 1H), 6.92-6.96 (m, 3H), 7.13 (t, J=7.8, Hz, 1H), 7.48 (dt, J=8.8, 2.1 Hz, 2H) ppm. MS (DCl/NH3) m/z 295 (M+H)+.

Workup

  1. washwashed with brine (2×5 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as oil (230 mg, yield, 78%)

Sources & evidence

ORD record
ord-8fd1fcbc95724edba562c8915281c22d
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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