Benzo(B)Thiophene-2-Boronic Acid → HCID 78426269, compound

HRID 2205204Notes

Reaction equation

HRID 2205204 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[CH:9]=[C:10]([NH:11][CH:12]3[CH2:14][CH2:13]3)[C:5]2=[N:4][CH:3]=1.B(O)(O)[C:27]1[S:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:35]1[C:27]([C:2]2[N:6]3[N:7]=[C:8]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=4)[CH:9]=[C:10]([NH:11][CH:12]4[CH2:14][CH2:13]4)[C:5]3=[N:4][CH:3]=2)=[CH:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]1=2

Participants

6

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 90387975HCID 90387975, compound

Product 1

HCID 78426269HCID 78426269, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-N8-cyclopropyl-N6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazine-6,8-diamine (66 mg, 0.163 mmol, 1.0 equiv) in acetonitrile (1.63 mL), was added benzo[b]thiophen-2-yl-2-boronic acid (58 mg, 0.327 mmol, 2.0 equiv), bis(triphenylphosphine)palladium(II) chloride (11 mg, 0.0163 mmol, 0.1 equiv), then sodium carbonate (1.63 mL, 1.0 M aqueous solution, 10 equiv). The reaction mixture was irradiated at 150° C. for 10 min. Purification by column chromatography gave 26 mg of the brown solid, 34%.

Workup

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

Sources & evidence

ORD record
ord-c1685368f158438aa507e1d38866f068
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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