Diisopropylethylamine → 1-(6-Bromo-3-methoxy-2-pyridyl)-1,4-diazepan-6-ol

HRID 57908Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6](F)[C:5]([O:9][CH3:10])=[CH:4][CH:3]=1.Br.Br.[NH:13]1[CH2:19][CH:18]([OH:20])[CH2:17][NH:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(O)(C)C>[Br:1][C:2]1[N:7]=[C:6]([N:13]2[CH2:19][CH:18]([OH:20])[CH2:17][NH:16][CH2:15][CH2:14]2)[C:5]([O:9][CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-bromo-2-fluoro-3-methoxy-pyridine (2.660 mmol; 547.9 mg), 1,4-diazepan-6-ol dihydrobromide (3.989 mmol; 1109 mg), and N,N′-diisopropylethylamine (10.64 mmol; 1389 mg; 1.87 mL) in Isopropanol (10 mL) in a sealed pressure vial was heated at 100° C. overnight. The mixture was cooled to room temperature and concentrated. The residue was purified on silica eluted with 0 to 10% MeOH in DCM to afford 1-(6-bromo-3-methoxy-2-pyridyl)-1,4-diazepan-6-ol (301.2 mg, 37%).

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated
customThe residue was purified on silica
washeluted with 0 to 10% MeOH in DCM

Sources & evidence

ORD record: ord-2bae2907da894f6fa00b80858618068b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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