Boron tribromide → 4-Hydroxy-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)piperidin-4-yl]-amide

HRID 1929233Notes

Reaction equation

HRID 1929233 reaction equation
[N:1]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[C:25]([O:28]C)[CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[N:1]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[C:25]([OH:28])[CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 111769984-Methoxy-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)piperidin-4-yl]-amide

Product 1

HCID 596001244-Hydroxy-1H-indole-2-carboxylic acid [1-(2-azepan-1-yl-ethyl)piperidin-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The methoxy derivative from example 1 (100 mg, 0.25 mmol) is dissolved in 5 ml of DCM. A solution of BBr3 (1M in DCM, 2.5 ml, 2.5 mmol) is added and the mixture is stirred for 18 hours. It is then poured onto ice and washed with EtOAc (30 ml). The pH of the water layer is adjusted to 9 and extracted twice with EtOAc. The organic layers are combined washed with brine, dried over anhydrous sodium sulfate and evaporated.

Workup

  1. additionIt is then poured onto ice
  2. washwashed with EtOAc (30 ml)
  3. extractionextracted twice with EtOAc
  4. washThe organic layers are combined washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0998919ce06344ff983618c14b9cedc2
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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