Potassium Carbonate → HCID 59496692, compound

HRID 449328Notes

Reaction equation

HRID 449328 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8171545-Bromopyridine-2-carbonitrileHCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59496692HCID 59496692, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 7-bromo-1,2,3,4-tetrahydroisoquinoline (0.30 g, 1.4 mmol), 5-bromopyridine-2-carbonitrile (0.28 g, 1.5 mmol) and potassium carbonate (0.39 g, 2.8 mmol) in dimethyl sulfoxide (2.0 mL) was heated at 160° C. for 2 h. After cooled to r.t., the mixture was quenched with water (10 mL), and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with 30% ethyl acetate in hexanes to afford the desired product (0.15 g, yield: 34%). Analytic LCMS (M+H)+: m/z=314.2/316.2.

Workup

  1. temperatureAfter cooled to r.t.
  2. customthe mixture was quenched with water (10 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on a silica gel column with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0784cd0c56c94e90bf37b4f14ba5f392
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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