Boron tribromide → 2-ethyl-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamide

HRID 985280Notes

Reaction equation

HRID 985280 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14]C)=[CH:11][CH:12]=2)[N:7]([CH3:16])[C:6]=1[CH2:17][CH3:18])=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[N:7]([CH3:16])[C:6]=1[CH2:17][CH3:18])=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 207677942-Ethyl-6-methoxy-1-methyl-1H-indole-3-carboxylic acid methylamide

Product 1

HCID 221436512-ethyl-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-ethyl-6-methoxy-1-methyl-1H-indole-3-carboxylic acid methylamide 73f (0.267 g, 1.08 mmole) in 15 ml CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 3.25 ml, 3.25 mmole). The reaction mixture was stirred at room temperature for 2 h, quenched with saturated NH4OH to make pH˜10. The mixture was diluted with H2O and extracted with 10% CH3OH in CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The residue purified by flash column chromatography (3-5% CH3OH in CH2Cl2) to give pale yellow color solid (0.170 g, 68%). 1H NMR (CDCl3) δ7.40 (1H, d, J=8.5 Hz), 6.65 (1H, s), 6.59 (1H, d, J=8.5 Hz), 3.53 (3H, s), 3.28 (2H, q, J=7.5 Hz), 2.82 (3H, s), 1.13 (3H, t, J=7.5 Hz). ESIMS (MH+): 233.15.

Workup

  1. customquenched with saturated NH4OH
  2. additionThe mixture was diluted with H2O
  3. extractionextracted with 10% CH3OH in CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue purified by flash column chromatography (3-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-08b0174ab1e74cb0b5cfd4895d6dbf39
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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