2,2-Dimethylethenylboronic acid → HCID 59314267, compound

HRID 1047904Notes

Reaction equation

HRID 1047904 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19](Br)[C:18]=2[CH3:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH3:26][C:27]([CH3:32])=[CH:28]B(O)O>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:26]=[C:27]([CH3:32])[CH3:28])[C:18]=2[CH3:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 27632992,2-Dimethylethenylboronic acidHCID 59314325HCID 59314325, compound

Product 1

HCID 59314267HCID 59314267, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 2-(3-bromo-2-methylbenzoylamino)indan-2-carboxylic acid ethyl ester (293) (402 mg-1 mmol) and 2-methyl-1-propenylboronic acid (200 mg, 2 mmol, 2 eq) in dry DMF (20 mL) and saturated NaHCO3 (5 mL) is degassed for 10 min and then treated with tetrakis(triphenylphosphine)palladium(0) (400 mg). The mixture is stirred at 110° C. for 5 h. The reaction is cooled and the DMF removed in vacuo and the residue diluted with water (80 mL). The aqueous is filtered through celite and extracted with EtOAc (3×50 mL). The organic extracts are washed with water (2×30 mL) and brine (2×30 mL), and dried over MgSO4. The organic phase is then concentrated in vacuo and purified by flash chromatography (120 g silica gel, 30% EtOAc in heptane) to give pale yellow oil (350 mg, 92%).

Workup

  1. customis degassed for 10 min
  2. additiontreated with tetrakis(triphenylphosphine)palladium(0) (400 mg)
  3. temperatureThe reaction is cooled
  4. customthe DMF removed in vacuo
  5. additionthe residue diluted with water (80 mL)
  6. filtrationThe aqueous is filtered through celite
  7. extractionextracted with EtOAc (3×50 mL)
  8. washThe organic extracts are washed with water (2×30 mL) and brine (2×30 mL)
  9. dry with materialdried over MgSO4
  10. concentrationThe organic phase is then concentrated in vacuo
  11. custompurified by flash chromatography (120 g silica gel, 30% EtOAc in heptane)

Sources & evidence

ORD record
ord-a4daee93cad14a5e8a00b2ff62865dfd
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…