Potassium Carbonate → HCID 78427497, compound

HRID 2205230Notes

Reaction equation

HRID 2205230 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[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+].[CH3:68][O:69][C:70]1[CH:71]=[C:72]([CH:74]=[CH:75][C:76]=1[O:77][CH3:78])[NH2:73]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:68][O:69][C:70]1[CH:71]=[C:72]([NH:73][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[S:19][C:14]5=[CH:15][N:16]=[CH:17][CH:18]=[C:13]5[CH:12]=4)=[CH:9][N:10]=3)[N:7]=2)[CH:74]=[CH:75][C:76]=1[O:77][CH3:78]

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 90387765HCID 90387765, compound

Product 1

HCID 78427497HCID 78427497, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(thieno[2,3-c]pyridin-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.174 mmol, 1.0 equiv), xantphos (20 mg, 0.0349 mmol, 0.2 equiv), palladium acetate (4 mg, 0.0174 mmol, 0.1 equiv), and potassium carbonate (482 mg, 3.49 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (35 mg, 0.227 mmol, 1.3 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 38 mg, of the yellow solid, 54%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave 38 mg

Sources & evidence

ORD record
ord-a3282735458f415d8c44b4a665592225
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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