5-Methyl-2-furylmethylamine → (5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

HRID 1669699Notes

Reaction equation

HRID 1669699 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](Cl)=[N:7]2.[CH3:13][C:14]1[O:18][C:17]([CH2:19][NH2:20])=[CH:16][CH:15]=1>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:20][CH2:19][C:17]1[O:18][C:14]([CH3:13])=[CH:15][CH:16]=1)=[N:7]2

Participants

3

Reactant 2

HCID 27246835-Methyl-2-furylmethylamineHCID 142210335-Bromo-2-chloroquinoline

Product 1

HCID 67333430(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

Procedure

5-Bromo-2-chloroquinoline (CAS 99455, 2.2 g, 9 mmol) and 5-methyl-2-furanmethanamine (2.2 g, 20 mmol) were stirred in a sealed tube at 120° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient). (5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine was obtained as a light brown solid (2.67 g, 92%), MS: m/e =317.1 and 319.0 (M+H+).

Workup

  1. customThe reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-5869f8be4e3e4aceb3ab378736bfe364
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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