Potassium Carbonate → HCID 90388244, compound

HRID 2205209Notes

Reaction equation

HRID 2205209 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:20][CH3:21])[CH:18]=[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:17]1[CH:18]=[CH:19][C:13]2[CH:12]=[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)[S:15][C:14]=2[CH:16]=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 90388376HCID 90388376, compound

Product 1

HCID 90388244HCID 90388244, compoundYield 75%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(6-methoxybenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (82 mg, 0.260 mmol, 1.0 equiv), xantphos (30 mg, 0.0519 mmol, 0.2 equiv), palladium acetate (6 mg, 0.0260 mmol, 0.1 equiv), and potassium carbonate (718 mg, 5.19 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (48 mg, 0.312 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 77 mg, 0.195 mmol of the yellow solid, 75%.

Workup

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

Sources & evidence

ORD record
ord-b6c9e6fcf1cf4199b02efda4a7eaa69e
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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