Potassium Carbonate → HCID 78427376, compound

HRID 2205239Notes

Reaction equation

HRID 2205239 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:18]4[C:17]([OH:20])=[CH:16][N:15]=[CH:14][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:19][C:18]5[C:17]([OH:20])=[CH:16][N:15]=[CH:14][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 90388219HCID 90388219, compound

Product 1

HCID 78427376HCID 78427376, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(6-chloroimidazo[1,2-b]pyridazin-3-yl)thieno[3,2-c]pyridin-7-ol (50 mg, 0.165 mmol, 1.0 equiv), xantphos (19 mg, 0.0330 mmol, 0.2 equiv), palladium acetate (4 mg, 0.0165 mmol, 0.1 equiv), and potassium carbonate (456 mg, 3.30 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (38 mg, 0.248 mmol, 1.5 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 30 mg, of the brown solid, 43%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave 30 mg

Sources & evidence

ORD record
ord-a71ad8062c7f45109ce467baa6d6aa89
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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