o-Chloranil → HCID 59367710, compound

HRID 515571Notes

Reaction equation

HRID 515571 reaction equation
C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl.[Br:13][C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:24][CH2:23]3)=[N:18][N:17]2[C:33]=1[CH:34]1[CH:39]=[CH:38][N:37](C(OCC)=O)[N:36]=[CH:35]1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.ClCCl>[Br:13][C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:24][CH2:23]3)=[N:18][N:17]2[C:33]=1[C:34]1[CH:39]=[CH:38][N:37]=[N:36][CH:35]=1

Participants

6

Reactant 2

HCID 73252o-ChloranilHCID 59367706HCID 59367706, compound

Product 1

HCID 59367710HCID 59367710, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

0.101 g of ortho-chloranil (0.41 mmol) in solution in 1 ml of toluene is added to a mixture of 0.16 g (0.32 mmol) of ethyl 4-[2-bromo-6-(4-pyrrolidin-1-ylpiperidin-1-yl)imidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate in 4 ml of chloroform. The mixture is stirred at ambient temperature for 1 hour and then diluted with 40 ml of dichloromethane. The solution is washed with 2 ml of a 2N aqueous solution of sodium hydroxide and then with a saturated solution of sodium chloride. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure after the addition of silica gel. The evaporation residue is loaded onto a silica gel column and the product is purified by chromatography on a silica gel column, elution being carried out with a mixture of 0 to 10% of methanol in dichloromethane. 0.080 g of product is thus isolated.

Workup

  1. washThe solution is washed with 2 ml of a 2N aqueous solution of sodium hydroxide
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionafter the addition of silica gel
  5. customthe product is purified by chromatography on a silica gel column, elution
  6. additionbeing carried out with a mixture of 0 to 10% of methanol in dichloromethane

Sources & evidence

ORD record
ord-fe1a9fa1fed74339ae503268b3c82072
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

Loading…