Potassium Carbonate → HCID 78427497, compound

HRID 2205232Notes

Reaction equation

HRID 2205232 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[S:29][C:28]5[CH:27]=CN=[CH:24][C:23]=5[CH:22]=4)=[CH:19][N:20]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].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+].COC1C=[C:82](C=CC=1OC)[NH2:83]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[S:29][C:28]5=[CH:27][N:83]=[CH:82][CH:24]=[C:23]5[CH:22]=4)=[CH:19][N:20]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

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 90388586HCID 90388586, compound

Product 1

HCID 78427497HCID 78427497, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a solution of N-(3,4-dimethoxyphenyl)-3-(thieno[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-amine (44 mg, 0.153 mmol, 1.0 equiv), xantphos (18 mg, 0.0306 mmol, 0.2 equiv), palladium acetate (3 mg, 0.0153 mmol, 0.1 equiv), and potassium carbonate (424 mg, 3.07 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (28 mg, 0.184 mmol, 1.2 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 38 mg, of the yellow solid, 62%.

Workup

  1. customPurification by column chromatography
  2. wash2% methanol in dichloromethane elution
  3. customgave 38 mg

Sources & evidence

ORD record
ord-c1b1501b78f54852bbd46cd64efd488b
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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