2-(2-Bromoethyl)pyridine → HCID 68212661, compound

HRID 2202156Notes

Reaction equation

HRID 2202156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>ClCCl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:15][CH2:14]3)[N:10]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 129138582-(2-Bromoethyl)pyridineHCID 67470977HCID 67470977, compound

Product 1

HCID 68212661HCID 68212661, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of INTERMEDIATE 5 (30 mg, 0.089 mmol) in dichloromethane (0.4 mL) was added 2-(2-bromoethyl)pyridine (28.4, 0.107 mmol). The mixture was stirred at 60° C. overnight, and then cooled to room temperature. The mixture was diluted with EtOAc, and washed with water. The organic layer was separated, dried and concentrated. The resulting residue was purified by preparative TLC (using 2 M NH3 in MeOH/MeOH/DCM/0.05 mL/5 mL/9.5 mL) to give the title compound. LC-MS m/z 443.17 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue was purified by preparative TLC (using 2 M NH3 in MeOH/MeOH/DCM/0.05 mL/5 mL/9.5 mL)

Sources & evidence

ORD record
ord-548575cb3a634c118f9d8ec204630b3b
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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