Sodium Carbonate → HCID 90388460, compound

HRID 2205221Notes

Reaction equation

HRID 2205221 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.[CH3:22][O:23][C:24]1[C:29]2[S:30][CH:31]=[CH:32][C:28]=2[C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=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>[CH3:22][O:23][C:24]1[C:29]2[S:30][CH:31]=[CH:32][C:28]=2[C:27]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90387847HCID 90387847, compoundHCID 90388018HCID 90388018, compound

Product 1

HCID 90388460HCID 90388460, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3 3-bromo-N-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine (43 mg, 0.123 mmol, 1.0 equiv) in acetonitrile (1.23 mL) was added 2-(7-methoxybenzo[b]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (46 mg, 0.160 mmol, 1.3 equiv), bis(triphenylphosphine)palladium(II)dichloride (9 mg, 0.0123 mmol, 0.1 equiv), then sodium carbonate (1.23 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 30 mg of the yellow solid, 56%.

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-b9e860d2d2c5454d8869255403242366
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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