Water → 3-Bromo-6,6-dimethyl-8-(piperidin-4-yloxy)-5,6-dihydro-benzo[b]carbazol-11-one

HRID 61837Notes

Reaction equation

HRID 61837 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:34])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH:22]5[CH2:27][CH2:26][N:25](C(=O)C(F)(F)F)[CH2:24][CH2:23]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[OH-].[K+].O>C1COCC1.CO>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:34])[C:8]4[CH:20]=[CH:19][C:18]([O:21][CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86663823HCID 86663823, compound

Product 1

HCID 668349073-Bromo-6,6-dimethyl-8-(piperidin-4-yloxy)-5,6-dihydro-benzo[b]carbazol-11-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-6,6-dimethyl-8-[1-(2,2,2-trifluoro-acetyl)-piperidin-4-yloxy]-5,6-dihydro-benzo[b]carbazol-11-one (Compound T6-1, 28.0 mg, 52.3 μmol) was dissolved in THF (1.00 mL) and methanol (0.50 mL), added with aqueous solution of potassium hydroxide (1.00 mL, 20 wt %), and stirred at room temperature for 1 hr. The reaction solution was added to water, and extracted with mixture solution of chloroform and methanol, and dried over sodium sulfate. Then, after filtering and concentration under reduced pressure, 3-bromo-6,6-dimethyl-8-(piperidin-4-yloxy)-5,6-dihydro-benzo[b]carbazol-11-one was obtained as a crude product.

Workup

  1. extractionextracted with mixture solution of chloroform and methanol
  2. dry with materialdried over sodium sulfate
  3. filtrationThen, after filtering
  4. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-7bd95a85075e4d15ad8a60501d8d7b03
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

Loading…