Sodium Carbonate → HCID 69307018, compound

HRID 2250654Notes

Reaction equation

HRID 2250654 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[C:10]2[N:11]([C:13]([CH2:16][CH3:17])=[CH:14][CH:15]=2)[N:12]=1)(=O)=O.[O:32]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH2:16]([C:13]1[N:11]2[N:12]=[C:7]([C:33]3[O:32][CH:36]=[CH:35][CH:34]=3)[C:8]([S:26]([CH3:29])(=[O:27])=[O:28])=[C:9]([C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[C:24]#[N:25])[C:10]2=[CH:15][CH:14]=1)[CH3:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 86597479HCID 86597479, compound

Product 1

HCID 69307018HCID 69307018, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-(3-cyanophenyl)-7-ethyl-3-(methylsulfonyl)pyrrolo[1,2-b]pyridazin-2-yl trifluoromethanesulfonate (50.0 mg), 3-furylboronic acid (23.6 mg), dichlorobis(triphenylphosphine)palladium (3.71 mg), and 2 N sodium carbonate (44.8 mg in 0.2 mL of water) in dioxane was stirred for 20 minutes at 85° C. The mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried, and evaporated. Preparative thin layer chromatography (EtOAc-hexane=1-1) afforded 3-[7-ethyl-2-(2-furyl)-3-(methylsulfonyl)pyrrolo[1,2-b]pyridazin-4-yl]benzonitrile as an orange solid (11.5 mg).

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-d25e16c31c30461fbb5fbf7388b1251f
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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