Toluene → HCID 66876371, compound

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].C1(C)C=CC=CC=1>ClCCl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:28]=[CH:27][CH:26]=[C:11]([CH:12]=[C:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

Procedure

tert-Butyl 4-(3-(5-bromopyrimidin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.285 g, 0.629 mmol) was suspended in dichloromethane (4 mL) and treated with trifluoroacetic acid (2 mL). The reaction mixture was stirred at ambient temperature for 3 h. Toluene was added and the reaction was concentrated in vacuo. After evaporating again from toluene, the residue was dried in vacuo to afford the title compound (0.385 g, quantitative yield based on 2.3 eq trifluoroacetic acid) as an orange oil. This material was dissolved in acetonitrile (3 mL) and used in the next step.