Ethyl Acetate → HCID 67071912, compound

HRID 2094208Notes

Reaction equation

HRID 2094208 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][C:10](Br)=[C:9]([O:18][CH3:19])[CH:8]=2)=[O:3].[CH:20](B1OC(C)(C)C(C)(C)O1)=[CH2:21].C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCOCC1.O.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][C:10]([CH:20]=[CH2:21])=[C:9]([O:18][CH3:19])[CH:8]=2)=[O:3]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67071846HCID 67071846, compound

Product 1

HCID 67071912HCID 67071912, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 2-aminocarbonylamino-5-bromo-6-methoxyindole-3-carboxamide (Compound No.7-1, 86 mg, 0.26 mmol), vinylboronic acid pinacol ester (121 μL, 0.40 mmol), tetrakis(triphenylphosphine)palladium(0) (32 mg, 0.027 mmol) and sodium hydrogen carbonate (56 mg, 0.66 mmol) in 1,4-dioxane-water solution (3:1, 15 mL) was stirred overnight at 110° C. under argon atmosphere. After cooling, ethyl acetate (20 mL) and brine (15 mL) were added and separated. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (4 mg) as a dark green solid (6%).

Workup

  1. temperatureAfter cooling
  2. customseparated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c69cae591dea412999da5e59c321f5d5
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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