Potassium Carbonate → HCID 131722755, compound

HRID 1383857Notes

Reaction equation

HRID 1383857 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][CH2:8][C:9]#[C:10][CH2:11]Cl.[CH:13]1([C:17]2[C:22]([O:23]CC#N)=[N:21][N:20]3[C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:28][N:29]=[C:19]3[CH:18]=2)[CH2:16][CH2:15][CH2:14]1>CN(C=O)C>[Cl:7][CH2:8][C:9]#[C:10][CH2:11][O:23][C:22]1[C:17]([CH:13]2[CH2:16][CH2:15][CH2:14]2)=[CH:18][C:19]2[N:20]([C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:28][N:29]=2)[N:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131821,4-Dichloro-2-butyneHCID 9926519HCID 9926519, compound

Product 1

HCID 131722755HCID 131722755, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (311 mg, 2.2 mmol) and 1,4 dichloro-2-butyne (275 mg, 2.2 mol) in DMF (3 ml) were heated to 50° C. prior to the dropwise addition of the product from Example 185, Step a (200 mg, 0.75 mmol) in DMF (2 ml). The reaction mixture was left to stir for 2 hours. Cooled and partitioned (ethyl acetate/water). The organic layer was washed (H2O, brine), dried MgSO4) and evaporated in vacuo. Purified via silica gel chromatography using 50/50 ethyl acetate/hexane to elute. 1H NMR (250 MHz, CDCl3) δ1.93 (1 H, m), 2.11-2.16 (3 H, m), 2.42 (2 H, m), 4.2 (2 H, m), 5.10 (2 H, m), 7.50-7.59 (3 H, m), 7.84 (1 H, s), 8.47 (2 H, m).

Workup

  1. waitThe reaction mixture was left
  2. temperatureCooled
  3. custompartitioned (ethyl acetate/water)
  4. washThe organic layer was washed (H2O, brine), dried MgSO4) and
  5. customevaporated in vacuo
  6. customPurified via silica gel chromatography
  7. washto elute

Sources & evidence

ORD record
ord-0d4003ad95f9474e898341baad35912b
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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