2-Methoxybenzylamine → 5-(4-Fluorobenzyloxy)-quinolin-2-yl-(2-methoxy-benzyl)-amine

HRID 1170123Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[N:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH:10]=[CH:11][C:2]([NH:26][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[O:22][CH3:21])=[N:3]3)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 812922-Methoxybenzylamine

HCID 866194962-Chloro-5-(4-fluoro-benzyloxy)-quinoline

Product 1

HCID 673346515-(4-Fluorobenzyloxy)-quinolin-2-yl-(2-methoxy-benzyl)-amine

Procedure

2-Chloro-5-(4-fluoro-benzyloxy)-quinoline (100 mg, 0.35 mmol) and 2-methoxybenzylamine (144 mg, 1.05 mmol) were stirred in a sealed tube at 150° C. for 16 hours. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient). 5-(4-Fluorobenzyloxy)-quinolin-2-yl-(2-methoxy-benzyl)-amine was obtained as a yellow oil (57 mg, 42%), MS: m/e=389.3 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-a050bf34850b4d77aea020c8fa6f4d4b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825253B2

Reaction notes

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