Potassium Carbonate → HCID 11337039, compound

HRID 2115195Notes

Reaction equation

HRID 2115195 reaction equation
[C:1]1([C:7]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[C:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31]>C(#N)C>[CH3:31][C:30]([CH3:32])=[CH:29][CH2:28][N:15]1[CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][C:8](=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)[CH2:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 11471554HCID 11471554, compound

Product 1

HCID 11337039HCID 11337039, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 100 mg (355 μmol) of 3-(phenyl-thiophen-3-yl-methylene)-8-aza-bicyclo[3.2.1]octane in 1 mL of acetonitrile was added 98 mg (710 μmol) of K2CO3 and 41 μL (355 μmol) of 4-bromo-2-methyl-2-butene at room temperature. The reaction mixture was allowed to stir overnight at room temperature. Next day, the crude was filtered and washed with acetonitrile. The combined filtrates were concentrated. The concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column using a gradient of 0.1% TFA/water to 5% water/0.1% TFA/acetonitrile). The eluent was evaporated to yield the title compound as a white solid; MS m/z (MH+) 350; 1H NMR 300 MHz (MeOD-d4) δ 6.87-7.39 (m, 8H), 5.35 (t, 1H), 3.94-4.00 (m, 2H), 3.29-3.31 (m, 2H), 2.58-2.89 (m, 4H), 1.62-2.25 (m, 10H).

Workup

  1. filtrationNext day, the crude was filtered
  2. washwashed with acetonitrile
  3. concentrationThe combined filtrates were concentrated
  4. customThe concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column
  5. customThe eluent was evaporated

Sources & evidence

ORD record
ord-ee0e11c4f34b42c6acce7d9df13f3bde
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

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