2-Chloroquinoline → 2-((3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methoxy)quinoline

HRID 718713Notes

Reaction equation

[Br:1][C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][OH:18].Cl[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.[H-].[Na+]>CN(C)C=O>[Br:1][C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][O:18][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 83a (1 g, 3 mmol) and 2-chloroquinoline (780 mg, 4.76 mmol) in N,N-dimethylformamide (20 mL), 60% sodium hydride (200 mg, 5.00 mmol) was added in portions. The reaction mixture was stirred overnight at 80° C. and quenched by the addition of 20 mL of water. The solids were collected by filtration to afford compound 83b as a white solid. Mass Spectrum (LCMS, ESI pos.) Calcd. For C20H18BrN5O2: 440.1 (M+H). Found 440.2.

Workup

customquenched by the addition of 20 mL of water
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-8688e3a8c0cc4af5bffad83bdaff1cd9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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