Hydrogen Peroxide → 6-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796635Notes

Reaction equation

HRID 1796635 reaction equation
OO.B(F)(F)F.CC[O:9]CC.OC([C:16]1[C:17]([CH3:41])=[C:18]2[C:23]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[C:22]([C:38]#[N:39])[CH:21]=[N:20][N:19]2[CH:40]=1)(C)C>C(Cl)Cl>[OH:9][C:16]1[C:17]([CH3:41])=[C:18]2[C:23]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:29][CH:30]=3)=[C:22]([C:38]#[N:39])[CH:21]=[N:20][N:19]2[CH:40]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 221796836-(1-Hydroxy-1-methyl-ethyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Product 1

HCID 221796716-Hydroxy-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

34% H2O2 (53 μl, 0.058 mmol) was added to CH2Cl2 (3 ml) at −10° C., then BF3.Et2O (0.64 ml, 5.0 mmol) was added. After the mixture was stirred at −10° C. for 20 min, a suspension of 396 (165 mg, 0.42 mmol) in CH2Cl2 (2 ml) was added. The reaction was stirred at −10° C. for 5 min, then quenched with aq Na2SO3, extracted with EtOAc. The organic layer was dried, concentrated and purified by silica gel flash column chromatography to give 397A (125 mg, 85%) (10% EtOAc—CH2Cl2).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred at −10° C. for 5 min
  3. customquenched with aq Na2SO3
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-2a88b91133454ef98c505e5c118fd0ae
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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