2-(Chloromethyl)quinoline → 2-((4-(5-(Pyridin-4-yl)oxazol-4-yl)phenoxy)methyl)quinoline

HRID 33917

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.[F-].[Cs+].Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1>CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[CH:14][CH:13]=2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 4-(5-(pyridin4-yl)oxazol4-yl)phenol (90 mg, 0.38 mmol) in 1 mL of dry DMF was added CsF (115 mg, 0.76 mmol). After stirring for 0.5 h, 2-(chloromethyl)quinoline (67 mg, 0.38 mmol) was added and the reaction was heated at 80° C. for 48 h. Upon removal of DMF under vacuum, the residue was purified by PTLC (1:2 hexane/EtOAc) to give 29 mg (20%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ: 5.47 (s, 2H), 7.11 (m, 2H), 7.56 (m, 5H), 7.70 (d, 1H), 7.78 (t, 1H), 7.86 (d, 1H), 8.01 (s, 1H), 8.12 (d, 1H), 8.26 (d, 1H), 8.57 (d, (2H). MS m/z: 380 [M+1]+.

Workup

customUpon removal of DMF under vacuum
customthe residue was purified by PTLC (1:2 hexane/EtOAc)

Sources & evidence

ORD record: ord-d986365884614a968ab7c5004a05b7d6
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Linked notes

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