Potassium Carbonate → HCID 90387978, compound

HRID 2205233Notes

Reaction equation

HRID 2205233 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:13](=[N:14][CH:15]=[CH:16][CH:17]=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+].[CH3:68][O:69][C:70]1[CH:71]=[C:72]([CH:74]=[CH:75][C:76]=1[O:77][CH3:78])[NH2:73]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:68][O:69][C:70]1[CH:71]=[C:72]([NH:73][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[S:19][C:18]5[C:13](=[N:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=4)=[CH:9][N:10]=3)[N:7]=2)[CH:74]=[CH:75][C:76]=1[O:77][CH3:78]

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 90388025HCID 90388025, compound

Product 1

HCID 90387978HCID 90387978, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of 6-chloro-3-(thieno[3,2-b]pyridin-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.174 mmol, 1.0 equiv), xantphos (20 mg, 0.0348 mmol, 0.2 equiv), palladium acetate (4 mg, 0.0174 mmol, 0.1 equiv), and potassium carbonate (482 mg, 3.49 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (32 mg, 0.209 mmol, 1.2 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 35 mg, of the yellow solid, 50%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave 35 mg

Sources & evidence

ORD record
ord-8976aeefb2ee48fcbf9c5f0de154a91d
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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