Potassium Carbonate → HCID 136597126, compound

HRID 2205197Notes

Reaction equation

HRID 2205197 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([O:20][CH3:21])=[C:15]([O:22][CH3:23])[CH:14]=4)=[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:76](=[O:79])([O-])[O-].[K+].[K+].CO[C:84]1[CH:85]=[C:86]([CH:88]=[CH:89][C:90]=1[O:91][CH3:92])[NH2:87]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:22][CH3:23])[NH:12][C:11]([C:8]1[N:6]3[N:7]=[C:2]([NH:87][C:86]4[CH:88]=[CH:89][C:90]([O:91][CH3:92])=[C:84]([O:79][CH3:76])[CH:85]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=1)=[CH:19]2

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 90388062HCID 90388062, compound

Product 1

HCID 136597126HCID 136597126, compoundYield 31.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(5,6-dimethoxy-1-tosyl-1H-indol-2-yl)imidazo[1,2-b]pyridazine (68 mg, 0.141 mmol, 1.0 equiv), xantphos (16 mg, 0.0282 mmol, 0.2 equiv), palladium acetate (3 mg, 0.0141 mmol, 0.1 equiv), and potassium carbonate (389 mg, 2.82 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (24 mg, 0.155 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 20 mg of the yellow solid.

Workup

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

Sources & evidence

ORD record
ord-8b97bacafc85492499885ac3ffbf702f
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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