Water → HCID 71253296, compound

HRID 1029014Notes

Reaction equation

HRID 1029014 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[CH:5]2.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1.O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:28][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[C:6]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 77230990HCID 77230990, compound

Product 1

HCID 71253296HCID 71253296, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A glass microwave reaction vessel was charged with 6-bromo-2-chloro-3-(tetrahydro-2H-pyran-4-yl)quinoline (1.46 g, 4.47 mmol) and (4-methoxyphenyl)methanamine (5.80 mL, 44.7 mmol) in N-methyl-2-pyrrolidinone (5.80 mL). The reaction mixture was stirred and heated in a microwave reactor at 130° C. for 180 min. The reaction mixture was poured into water and extracted with EtOAc and DCM. The combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material as a yellow oil. The crude material was purified by silica gel chromatography by eluting with 1:4 to 1:1 EtOAc in hexane, to provide 6-bromo-N-(4-methoxybenzyl)-3-(tetrahydro-2H-pyran-4-yl)quinolin-2-amine as yellow solid.

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with EtOAc and DCM
  3. washThe combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as a yellow oil
  8. customThe crude material was purified by silica gel chromatography
  9. washby eluting with 1:4 to 1:1 EtOAc in hexane

Sources & evidence

ORD record
ord-8992ec52e40f4a96b5062bef86ab8c01
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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