Potassium Carbonate → HCID 78426687, compound

HRID 2205214Notes

Reaction equation

HRID 2205214 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[CH:16]=[C:17]([O:24][CH3:25])[C:18]([O:22][CH3:23])=[C:19]([O:20][CH3:21])[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+].[CH3:74][O:75][C:76]1[CH:77]=[C:78]([CH:80]=[CH:81][C:82]=1[O:83][CH3:84])[NH2:79]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:19]1[C:13]2[CH:12]=[C:11]([C:8]3[N:6]4[N:7]=[C:2]([NH:79][C:78]5[CH:80]=[CH:81][C:82]([O:83][CH3:84])=[C:76]([O:75][CH3:74])[CH:77]=5)[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)[S:15][C:14]=2[CH:16]=[C:17]([O:24][CH3:25])[C:18]=1[O:22][CH3:23]

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 90387662HCID 90387662, compound

Product 1

HCID 78426687HCID 78426687, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(4,5,6-trimethoxybenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.133 mmol, 1.0 equiv), xantphos (15 mg, 0.0266 mmol, 0.2 equiv), palladium acetate (2 mg, 0.0133 mmol, 0.1 equiv), and potassium carbonate (367 mg, 2.66 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (20 mg, 0.133 mmol, 1.0 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave the product.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave the product

Sources & evidence

ORD record
ord-36441e35c6cc41d08ff91cd7cc44e50b
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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