Acetonitrile → N-[1-(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-1-methyl-ethyl]-acetamide

HRID 1798505Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14](O)([CH3:16])[CH3:15])[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:9]=2)[CH:5]=[N:6][CH:7]=1.[OH-:24].[Na+].[C:26](#[N:28])[CH3:27]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([NH:28][C:26](=[O:24])[CH3:27])([CH3:16])[CH3:15])[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-(5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-propan-2-ol (Example 2.80; step1) (1 eq, 0.135 mmol, 50 mg) in acetonitrile (2 ml) is added tetrafluoroboric acid diethyl ether complex (3.5 eq, 0.473 mmol, 0.06 ml) and the reaction mixture is heated at 85° C. overnight. The pH of the reaction mixture is adjusted to 8-9 by addition of sodium hydroxide (2M). The solution is dissolved in DCM and washed with water. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound; [M+H]+ 411/413

Workup

washwashed with water
washThe combined organic extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e564add6a80b4a4089ac927f528a45f2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343966B2

Reaction notes

Loading…