2-Methoxybenzylamine → HCID 68436248, compound

HRID 1170132Notes

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][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25]>>[F:19][C:16]1[CH:17]=[CH:18][C: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:25][CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[O:21][CH3:20])=[N:3]3)=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 812922-Methoxybenzylamine

HCID 59743616HCID 59743616, compound

Product 1

HCID 68436248HCID 68436248, compound

Procedure

2-Chloro-5-(4-fluoro-phenoxy)-quinoline (60 mg, 0.22 mmol) and 2-methoxybenzylamine (90 mg, 0.66 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->75:25 gradient). (5-(4-Fluoro-phenoxy)-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as a yellow oil (56 mg, 68%), MS: m/e=375.4 (M+H+).

Workup

customThe reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->75:25 gradient)

Sources & evidence

ORD record: ord-f75a623abec646259caf05d223d76eb8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825253B2

Reaction notes

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