Hydrogen Bromide → 9-Bromonoscapine

HRID 1968413

Reaction equation

HRID 1968413 reaction equation
[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BrH:31].O.[Br]>>[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[C:6]([Br:31])[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 275196NoscapineHCID 178514845HCID 178514845, compound

Product 1

HCID 102550819-BromonoscapineYield 82%

Conditions

Temperature
25 °C

Procedure

Targetin was synthesized using a four-step synthetic scheme, as illustrated below. Noscapine (1) was brominated by adding 48% hydrobromic acid and freshly prepared bromine water. The reaction mixture was stirred for 1 hr at 25° C., and basified to pH 10 to yield 9-bromonoscapine (2) in ˜82% yield. Refluxing compound 2 in dimethyl formamide with sodium azide and sodium iodide for 15 hrs gave the corresponding azido derivative (3), which when reduced with tin chloride in the presence of thiophenol and triethylamine in tetrahydrofuran for 2 hrs at 25° C. to provide 9-aminonoscapine (4) in ˜83% yield.

Workup

  1. customTargetin was synthesized

Sources & evidence

ORD record
ord-889d2a73c91f4c0191ea369640bb008f
Source dataset
uspto-grants-2013_04
Patent number
US08426398B2

Linked notes

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