Potassium Carbonate → HCID 67248560, compound

HRID 335783Notes

Reaction equation

HRID 335783 reaction equation
CN[C@H]1[C@H](NC)CCCC1.[CH2:11]=[C:12]1[C:21]2[C:22](=[O:26])[NH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]2[CH:17]=[CH:16][C:15]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:14][C:13]1=2.I[C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CS(C)=O>[CH2:11]=[C:12]1[C:21]2[C:22](=[O:26])[N:23]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)[CH:24]=[CH:25][C:20]=2[O:19][C:18]2[CH:17]=[CH:16][C:15]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:14][C:13]1=2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 67249010HCID 67249010, compound

Product 1

HCID 67248560HCID 67248560, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with (1R,2R)-diaminomethylcyclohexane (9.77 mg, 0.069 mmol), copper(I) iodide (8.72 mg, 0.046 mmol), 10-methylene-8-(pyridin-3-yl)-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one (0.066 g, 0.229 mmol), 4-iodotoluene (0.055 g, 0.252 mmol), potassium carbonate (0.063 g, 0.458 mmol), and DMSO (2.5 mL). The system was purged with argon and the tube was sealed. The mixture stirred in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 2 h. The reaction mixture was diluted with dichloromethane and filtered through a pad of celite. The filtrate was concentrated and partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 10-methylene-8-(pyridin-3-yl)-2-p-tolyl-2,10-dihydro-1H-chromeno[3,2-c]pyridin-1-one. MS m/z=379.0 [M+H]+. Calcd for C25H18N2O2: 378.4.

Workup

  1. customThe system was purged with argon
  2. customthe tube was sealed
  3. additionThe reaction mixture was diluted with dichloromethane
  4. filtrationfiltered through a pad of celite
  5. concentrationThe filtrate was concentrated
  6. custompartitioned between dichloromethane and water
  7. customThe aqueous phase was separated
  8. extractionextracted with dichloromethane
  9. washThe combined organic phases were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b2b9b69cd3904bf480498a627d7e7ea6
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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