Dabco → HCID 67544486, compound

HRID 2176180Notes

Reaction equation

HRID 2176180 reaction equation
I[C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C:13](=O)[CH2:12]2.N12CCN(CC1)CC2.S([O-])([O-])(=O)=O.[Mg+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][C:7]1[CH:6]=[CH:5][C:3]2[NH:4][C:13]3[CH:14]4[CH2:17][CH2:18][N:11]([C:12]=3[C:2]=2[CH:8]=1)[CH2:16][CH2:15]4

Participants

6

Reactant 4

HCID 9237DabcoHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 27640002-Iodo-4-methylaniline

Product 1

HCID 67544486HCID 67544486, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

2-Iodo-4-methylaniline (2.0 g, 8.58 mmol; prepared as described in J. Org. Chem. 1999, 64, 9650), quinuclidin-3-one hydrochloride (2.36 g, 14.6 mmol; Aldrich), palladium(II) acetate (145 mg, 0.646 mmol; Aldrich), 1,4-diazabicyclo[2.2.2]octane (DABCO; 3.47 g, 30.9 mmol; Aldrich) and magnesium sulfate (1.65 g, 13.7 mmol) were processed as described in Example 205A to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 1.52-1.62 (m, 2H), 1.92-2.05 (m, 2H), 2.39 (s, 3H), 2.55-2.69 (m, 2H), 3.22-3.29 (m, 2H), 3.40 (quintet, J=2.9 Hz, 1H), 6.85 (dd, J=8.2, 1.5 Hz, 1H), 7.21 (d, J=8.2 Hz, 1H), 7.34 (s, 1H); MS (APCI) m/z 213 (M+H)+.

Sources & evidence

ORD record
ord-6537d97f64b04605bd20488dc0458691
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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