Potassium Carbonate → HCID 90387897, compound

HRID 2205242Notes

Reaction equation

HRID 2205242 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]([CH3:20])=[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]([CH3:20])=[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 90388022HCID 90388022, compound

Product 1

HCID 90387897HCID 90387897, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(7-methylthieno[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazine (31 mg, 0.103 mmol, 1.0 equiv), xantphos (12 mg, 0.0206 mmol, 0.2 equiv), palladium acetate (2 mg, 0.0103 mmol, 0.1 equiv), and potassium carbonate (284 mg, 2.06 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (24 mg, 0.155 mmol, 1.5 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 20 mg, of the brown solid, 47%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave 20 mg

Sources & evidence

ORD record
ord-e1081005f7e84710b5585c624bc5be33
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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