Dabco → HCID 67543874, compound

HRID 2176178Notes

Reaction equation

HRID 2176178 reaction equation
I[C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[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:6]1[CH:7]=[CH:8][C:2]2[C:12]3[N:11]4[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]4)[C:13]=3[NH:4][C:3]=2[CH:5]=1

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 27366592-Iodo-5-methylaniline

Product 1

HCID 67543874HCID 67543874, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

2-Iodo-5-methylaniline (1.0 g, 4.29 mmol; Amfinecom), quinuclidin-3-one hydrochloride (1.24 g, 7.67 mmol; Aldrich), palladium(II) acetate (48 mg, 0.22 mmol; Aldrich), 1,4-diazabicyclo[2.2.2]octane (DABCO; 1.73 g, 15.4 mmol; Aldrich) and magnesium sulfate (0.88 g, 7.31 mmol) were processed as described in Example 205A to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 1.52-1.63 (m, 2H), 1.94-2.05 (m, 2H), 2.40 (s, 3H), 2.59-2.71 (m, 2H), 3.26 (ddd, J=12.2, 8.5, 4.3 Hz, 2H), 3.40 (quintet, J=2.9 Hz, 1H), 6.85 (d, J=7.3, 0.7 Hz, 1H), 7.14 (s, 1H), 7.42 (d, J=7.9 Hz, 1H); MS (DCI) m/z 213 (M+H)+.

Sources & evidence

ORD record
ord-b6b80488a32a4c97bda60806ec88c6ea
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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