Potassium Carbonate → HCID 78426971, compound

HRID 2205225Notes

Reaction equation

HRID 2205225 reaction equation
[S:1]1[C:5]([C:6]2[N:10]3[N:11]=[C:12](Cl)[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]3=[N:8][CH:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+].[CH3:70][O:71][C:72]1[CH:73]=[C:74]([CH:76]=[CH:77][C:78]=1[O:79][CH3:80])[NH2:75]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:1]1[C:5]([C:6]2[N:10]3[N:11]=[C:12]([NH:75][C:74]4[CH:76]=[CH:77][C:78]([O:79][CH3:80])=[C:72]([O:71][CH3:70])[CH:73]=4)[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]3=[N:8][CH:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 90387518HCID 90387518, compound

Product 1

HCID 78426971HCID 78426971, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(benzo[b]thiophen-2-yl)-6-chloro-7,8-dimethylimidazo[1,2-b]pyridazine (89 mg, 0.284 mmol, 1.0 equiv), xantphos (33 mg, 0.0567 mmol, 0.2 equiv), palladium acetate (6 mg, 0.0284 mmol, 0.1 equiv), and potassium carbonate (784 mg, 5.67 mmol, 20 equiv) in dioxane (5.00 mL) was added 3,4-dimethoxyaniline (52 mg, 0.340 mmol, 1.0 equiv) and heated to 100° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave the 60 mg of the brown solid, 49%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-9b8256e42c2241d39205ee5daa39acf6
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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