Sodium Carbonate → HCID 90388230, compound

HRID 2205215Notes

Reaction equation

HRID 2205215 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[F:22][C:23]1[CH:40]=[CH:39][C:26]2[S:27][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:29][C:25]=2[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:22][C:23]1[CH:40]=[CH:39][C:26]2[S:27][C:28]([C:2]3[N:6]4[N:7]=[C:8]([NH:11][C:12]5[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=5)[CH:9]=[CH:10][C:5]4=[N:4][CH:3]=3)=[CH:29][C:25]=2[CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 533986125-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzo[b]thiopheneHCID 90388018HCID 90388018, compound

Product 1

HCID 90388230HCID 90388230, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-N-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine (118 mg, 0.338 mmol, 1.0 equiv) in acetonitrile (3.38 mL) was added 2-(5-fluorobenzo[b]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (122 mg, 0.439 mmol, 1.3 equiv), bis(triphenylphosphine)palladium(II)dichloride (24 mg, 0.0338 mmol, 0.1 equiv), then sodium carbonate (3.38 mL, 1.0 M aqueous solution, 10 equiv). The reaction mixture was irradiated in the microwave at 150° C. for 10 min. Purification by column chromatography gave 100 mg of the brown solid, 70%.

Workup

  1. customThe reaction mixture was irradiated in the microwave at 150° C. for 10 min
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-00113cd579354f32906cc389a2549d7a
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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