Potassium Carbonate → HCID 90388494, compound

HRID 2205207Notes

Reaction equation

HRID 2205207 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[C:16]([CH3:20])=[CH:17][CH:18]=[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>[CH3:69][O:70][C:71]1[CH:72]=[C:73]([NH:74][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[S:15][C:14]5[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:13]=5[CH:12]=4)=[CH:9][N:10]=3)[N:7]=2)[CH:75]=[CH:76][C:77]=1[O:78][CH3:79]

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 90387861HCID 90387861, compound

Product 1

HCID 90388494HCID 90388494, compoundYield 116.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(7-methylbenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.167 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 (21 mg, 0.184 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, 0.195 mmol of the yellow solid, 58%.

Workup

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

Sources & evidence

ORD record
ord-f52c8253cf1e4c4f9eb47c59d0b99bfd
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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