Sodium Carbonate → HCID 90388062, compound

HRID 2205196Notes

Reaction equation

HRID 2205196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:7](B1OC(C)(C)C(C)(C)O1)=[CH:6]2.[Cl:33][C:34]1[CH:35]=[CH:36][C:37]2[N:38]([C:40](I)=[CH:41][N:42]=2)[N:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.[Pd]>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]2[N:38]([C:40]([C:7]3[N:8]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[C:9]4[C:5]([CH:6]=3)=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=4)=[CH:41][N:42]=2)[N:39]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 532498976-Chloro-3-iodoimidazo[1,2-b]pyridazineHCID 90388490HCID 90388490, compound

Product 1

HCID 90388062HCID 90388062, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5,6-dimethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole (120 mg, 0.262 mmol, 1.0 equiv) in acetonitrile (3.41 mL) was added 6-chloro-3-iodoimidazo[1,2-b]pyridazine (95 mg, 0.341 mmol, 1.3 equiv), palladium catalyst (25 mg, 0.0341 mmol, 0.1 equiv) and sodium carbonate (3.41 mL, 1.0 M, 10.0 equiv). The solution was stirred at 150° C. in the microwave for 10 minutes. Purification using column chromatography gave 80 mg of the yellow solid, 63%.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-8045c38c51ff49b9ae9020f15fbdec83
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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