Ethyl Acetate → HCID 58659623, compound

HRID 1676988Notes

Reaction equation

HRID 1676988 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH2:14])=[O:13])=[C:6]2[S:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)(=[O:17])=[O:16].B(Br)(Br)[Br:25].CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCl>[Br:25][CH2:20][CH2:19][N:18]([CH2:23][CH2:22][OH:21])[S:15]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=2)[NH:8][C:7]=1[C:12]([NH2:14])=[O:13])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10472353HCID 10472353, compound

Product 1

HCID 58659623HCID 58659623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-methoxy-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide (416 mg, 1.23 mmol) in 15 mL of dichloromethane at −78° C. was added boron tribromide solution (1 M in dichloromethane, 6.13 mmol). After 10 minutes the mixture was allowed to warm to room temperature, and stir for an additional 60 hours. The reaction was poured into a mixture of EtOAc and saturated aqueous NaHCO3 solution. The organic phase was washed with water and brine, dried with Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography through silica gel (3-10% MeOH/dichloromethane) provide the titled product, along with 5-hydroxy-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C13H17BrN3O5S (M+H+): 406.0067. Found 406.0081.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography through silica gel (3-10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-077db07852164fe496ab031425dbe141
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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