Potassium Carbonate → HCID 90387943, compound

HRID 2205219Notes

Reaction equation

HRID 2205219 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]([CH:16]=[O:17])=[CH:13][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+].[CH3:66][O:67][C:68]1[CH:69]=[C:70]([CH:72]=[CH:73][C:74]=1[O:75][CH3:76])[NH2:71]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:66][O:67][C:68]1[CH:69]=[C:70]([NH:71][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[S:15][C:14]([CH:16]=[O:17])=[CH:13][CH:12]=4)=[CH:9][N:10]=3)[N:7]=2)[CH:72]=[CH:73][C:74]=1[O:75][CH3:76]

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 90387451HCID 90387451, compound

Product 1

HCID 90387943HCID 90387943, compoundYield 34.7%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(6-chloroimidazo[1,2-b]pyridazin-3-yl)thiophene-2-carbaldehyde (200 mg, 0.758 mmol, 1.0 equiv), xantphos (88 mg, 0.152 mmol, 0.2 equiv), palladium acetate (17 mg, 0.0758 mmol, 0.1 equiv), and potassium carbonate (2.10 g, 1.52 mmol, 20 equiv) in dioxane (6.0 mL) was added 3,4-dimethoxyaniline (116 mg, 0.758 mmol, 1.0 equiv) and heated to 100° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave the 100 mg of the brown solid, 35%.

Workup

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

Sources & evidence

ORD record
ord-1cf05a57db3842b6a729516fda8a4ebe
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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