Potassium Carbonate → HCID 90387661, compound

HRID 2205212Notes

Reaction equation

HRID 2205212 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]4[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:13]=4[CH:12]=3)=[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+].[CH3:69][O:70][C:71]1[CH:72]=[C:73]([CH:75]=[CH:76][C:77]=1[O:78][CH3:79])[NH2:74]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:20][C:18]1[CH:17]=[CH:16][C:14]2[S:15][C:11]([C:8]3[N:6]4[N:7]=[C:2]([NH:74][C:73]5[CH:75]=[CH:76][C:77]([O:78][CH3:79])=[C:71]([O:70][CH3:69])[CH:72]=5)[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[CH:12][C:13]=2[CH:19]=1

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 90388403HCID 90388403, compound

Product 1

HCID 90387661HCID 90387661, compoundYield 91%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(5-methylbenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.168 mmol, 1.0 equiv), xantphos (19 mg, 0.0334 mmol, 0.2 equiv), palladium acetate (4 mg, 0.0167 mmol, 0.1 equiv), and potassium carbonate (461 mg, 3.34 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (28 mg, 0.167 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 42 mg, 0.152 mmol of the yellow solid, 60%.

Workup

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

Sources & evidence

ORD record
ord-573dbe112dfd4e129f8e294e048fac72
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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