3,4-Dimethoxyaniline → HCID 90388018, compound

HRID 2205201Notes

Reaction equation

HRID 2205201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].CC(C)([O-])C.[K+].[Br:18][C:19]1[N:23]2[N:24]=[C:25](Cl)[CH:26]=[CH:27][C:22]2=[N:21][CH:20]=1>C1COCC1>[Br:18][C:19]1[N:23]2[N:24]=[C:25]([NH:6][C:5]3[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:26]=[CH:27][C:22]2=[N:21][CH:20]=1

Participants

5

Reactant 3

HCID 227703,4-DimethoxyanilineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 90388018HCID 90388018, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4-dimethoxyaniline (178 mg, 1.16 mmol, 2.0 equiv) in THF (5 mL) was added potassium tert-butoxide (131 mg, 1.16 mmol, 2.0 equiv) and heated to 60° C. for 30 min. The reaction mixture was cooled to room temperature then 3-bromo-6-chloroimidazo[1,2-b]pyridazine (135 mg, 0.582 mmol, 1.0 equiv) was added and stirred at room temperature for 15 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 102 mg of the dark brown solid, 50%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customPurification by column chromatography
  3. wash2% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-45159484ff504b9093583937e81504e4
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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