Potassium Carbonate → HCID 90388542, compound

HRID 2205211Notes

Reaction equation

HRID 2205211 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]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][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+].[CH3:70][O:71][C:72]1[CH:73]=[C:74]([CH:76]=[CH:77][C:78]=1[O:79][CH3:80])[NH2:75]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:14]2[S:15][C:11]([C:8]3[N:6]4[N:7]=[C:2]([NH:75][C:74]5[CH:76]=[CH:77][C:78]([O:79][CH3:80])=[C:72]([O:71][CH3:70])[CH:73]=5)[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[CH:12][C:13]=2[CH:19]=1

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 90388326HCID 90388326, compound

Product 1

HCID 90388542HCID 90388542, compoundYield 59.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(5-methoxybenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (80 mg, 0.254 mmol, 1.0 equiv), xantphos (29 mg, 0.0506 mmol, 0.2 equiv), palladium acetate (6 mg, 0.0254 mmol, 0.1 equiv), and potassium carbonate (700 mg, 5.06 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (47 mg, 0.304 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 62 mg, 0.152 mmol of the yellow solid, 60%.

Workup

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

Sources & evidence

ORD record
ord-5082aada605e40a8a56ccbdd7e229970
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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