4-Methoxybenzylamine → 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine

HRID 1028933Notes

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]([I:13])=[CH:5]2.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)[C:6]([I:13])=[CH:5]2

Participants

Reactant 2

HCID 754524-Methoxybenzylamine

HCID 866768376-Bromo-2-chloro-3-iodoquinoline

Product 1

HCID 673456526-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine

Conditions

Temperature: 130 °C

Procedure

6-Bromo-2-chloro-3-iodoquinoline (1.0 g, 2.7 mmol) and neat 4-methoxybenzylamine (3.6 mL, 27.1 mmol) was combined in a microwave vial and heated in a microwave at 130° C. for 15 min. The reaction mixture was purified by silica flash chromatography (0-30% EtOAc/Hex) to give 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine as a yellow solid.

Workup

customThe reaction mixture was purified by silica flash chromatography (0-30% EtOAc/Hex)

Sources & evidence

ORD record: ord-eced43b58d884e6baa1a3d853801dd21
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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