Potassium Carbonate → HCID 90388164, compound

HRID 2205195Notes

Reaction equation

HRID 2205195 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[N:12]([CH3:22])[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=4)=[CH:9][N:10]=2)[N:7]=1.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+].[CH3:71][O:72][C:73]1[CH:74]=[C:75]([CH:77]=[CH:78][C:79]=1[O:80][CH3:81])[NH2:76]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:22])[C:11]([C:8]1[N:6]3[N:7]=[C:2]([NH:76][C:75]4[CH:77]=[CH:78][C:79]([O:80][CH3:81])=[C:73]([O:72][CH3:71])[CH:74]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=1)=[CH:19]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 90388134HCID 90388134, compound

Product 1

HCID 90388164HCID 90388164, compoundYield 96.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(5-methoxy-1-methyl-1H-indol-2-yl)imidazo[1,2-b]pyridazine (49 mg, 0.157 mmol, 1.0 equiv), xantphos (18 mg, 0.0313 mmol, 0.2 equiv), palladium acetate (4 mg, 0.0156 mmol, 0.1 equiv), and potassium carbonate (433 mg, 3.13 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (26 mg, 0.172 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 40 mg, 0.152 mmol of the yellow solid, 59%.

Workup

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

Sources & evidence

ORD record
ord-b5397c0c148249f4950194758ee25ae4
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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