Ethyl Acetate → HCID 10041978, compound

HRID 227484Notes

Reaction equation

HRID 227484 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])=[C:8]([C:12]([NH2:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CCOC(C)=O.C([O-])(O)=O.[Na+]>ClCCl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([S:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])=[C:8]([C:12]([NH2:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 103151296-Methoxy-3-(morpholine-4-sulfonyl)-1H-indole-2-carboxamide

Product 1

HCID 10041978HCID 10041978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-methoxy-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide from Example 5 (134 mg, 0.395 mmol) in 5 mL of dichloromethane at −78° C. was added boron tribromide solution (1 M in dichloromethane, 1.97 mmol). After 10 minutes the mixture was allowed to warm to room temperature, and stir for an additional 4 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. Trituration with chloroform gave the titled compound as a brown powder. HRMS (ES) exact mass calculated for C13H16N3O5S (M+H+): 326.0805. Found 326.0794.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fa43d8cb8e44ad29a095d51651dfccf
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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