Sodium Carbonate → HCID 59656659, compound

HRID 2054915Notes

Reaction equation

HRID 2054915 reaction equation
[NH2:1][C:2]1[C:3]2[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CC#N.O>[NH2:1][C:2]1[C:3]2[CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59656640HCID 59656640, compound

Product 1

HCID 59656659HCID 59656659, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-amino-5-bromo-benzo[b]thiophene-2-carboxylic acid amide (90 mg, 0.33 mmol) in DMF (5 mL) was added phenylboronic acid (1.2 eq., 50 mg) at room temperature, under nitrogen. The resulting mixture was degassed and placed under nitrogen after which time sodium carbonate (1.2 eq., 43 mg) and Pd(Ph3)4 (0.4 eq., 155 mg) were added. The reaction was degassed again and warmed to 80° C. overnight, under nitrogen. Upon cooling to room temperature, the reaction was concentrated to dryness and the remaining residue was purified via flash column chromatrography (5 g SiO2, 0-40% EtOAc/dichloromethane). The product-containing fractions were concentrated to give the product which was still contaminated. The brown solid was diluted with 1:1 CH3CN/H2O and the remaining solids were removed via filtration. The filtrate was re-purified using preparatory reverse phase HPLC to give 7.4 mg (8%) of the title compound as a white solid.

Workup

  1. customThe resulting mixture was degassed
  2. additionwere added
  3. customThe reaction was degassed again
  4. temperatureUpon cooling to room temperature
  5. concentrationthe reaction was concentrated to dryness
  6. customthe remaining residue was purified via flash column chromatrography (5 g SiO2, 0-40% EtOAc/dichloromethane)
  7. concentrationThe product-containing fractions were concentrated
  8. customto give the product which
  9. customthe remaining solids were removed via filtration
  10. customThe filtrate was re-purified

Sources & evidence

ORD record
ord-ac5fb41dc5cf49509c81ae2e23ceeea9
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

Loading…