Ethyl Acetate → HCID 49805203, compound

HRID 1020430Notes

Reaction equation

HRID 1020430 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21](Br)[C:20]=2[CH3:26])=[CH:12][CH:11]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:20]=2[CH3:26])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 49805202HCID 49805202, compound

Product 1

HCID 49805203HCID 49805203, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

45 mg of N-(2-aminophenyl)-4-((3-bromo-2-methylbenzamido) methyl)benzamide obtained in Example 68 (0.103 mmol), phenyl boronic acid (19 mg, 0.154 mmol), tetrakis(triphenylphosphin)palladium (7 mg, 0.006 mmol), and sodium bicarbonate (33 mg, 0.308 mmol) were dissolved in 5 mL of dioxane/H2O mixture (v/v, 4:1). The resulting mixture was subjected to microwave equipment (Biotage AB) for 20 min at 150° C. Ethyl acetate was added to the resulting mixture, dried with anhydrous magnesium sulfate, and filtered with Celite. The filtrate was dried under a reduced pressure, and subjected to a column chromatography (ethyl acetate:methanol=9:1 (v:v)). The resulting mixture was dissolved in ethanol and dried to obtain the title compound (23 mg, 52%).

Workup

  1. dry with materialdried with anhydrous magnesium sulfate
  2. filtrationfiltered with Celite
  3. customThe filtrate was dried under a reduced pressure
  4. dissolutionThe resulting mixture was dissolved in ethanol
  5. customdried

Sources & evidence

ORD record
ord-f663c66f507a40b08341f2b492aeeba9
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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