Ethyl Acetate → HCID 59451442, compound

HRID 1874796Notes

Reaction equation

HRID 1874796 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11]C)=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:13]([O:15]C)=[O:14].B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 22141396methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylate

Product 1

HCID 59451442HCID 59451442, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-Bromo-6-(methyloxy)-1H-indole-2-carboxylate (0.075 g, 0.26 mmol) was dissolved in CH2Cl2 (5 mL), cooled to 0° C. under nitrogen and BBr3 (1.0 M in CH2Cl2, 1.6 mL, 1.6 mmol) added dropwise. The reaction mixture was allowed to warm to RT and stirred overnight. Ice cold water (1 mL) and EtOAc (5 mL) were added. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.005 g, 7%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 13.06 (br. s., 1H), 11.63 (br. s., 1H), 9.55 (s, 1H), 7.30 (d, 1H), 6.78 (d, 1H), 6.70 (dd, 1H). MS: m/z 256.13 (M+1).

Workup

  1. temperatureto warm to RT
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc (3×5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification

Sources & evidence

ORD record
ord-10b2871a33e043c29cc16d45c6a4c4d2
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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