N-bromobutanimide → HCID 57646773, compound

HRID 1022888Notes

Reaction equation

HRID 1022888 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[N:20][C:19]([Cl:25])=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:26]N1C(=O)CCC1=O>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:16]([Br:26])=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[N:20][C:19]([Cl:25])=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86629110HCID 86629110, compound

Product 1

HCID 57646773HCID 57646773, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

200 mg of 4-(3-Chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (178) were dissolved in 5 ml of CH3CN and heated to 85° C. Then a mixture of 148 mg of N-bromosuccinimide and 9 mg of AlBN was added as solid and the resulting mixture was heated to reflux for 1 h. The solvent was removed in vacuo and the residue subjected to flash column chromatography. The yield of the isolated product was 41% LCMS: detected mass: 441.03, Rt=2.41 min (Method #1)

Workup

  1. additionwas added as solid
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 1 h
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1367b694c6f24b2faf07950cecf65ace
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

Loading…