Toluene → 5-Bromo-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate

HRID 1666373Notes

Reaction equation

HRID 1666373 reaction equation
[Br:1][C:2]1[CH:3]=[CH: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>C(Cl)Cl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:28]=[CH:27][CH:26]=[C:11]([CH:12]=[C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 66876348HCID 66876348, compound

Product 1

HCID 668761435-Bromo-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-(5-bromopyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (1.36 g, 3.05 mmol) from Step 4 was dissolved in CH2Cl2 (15 mL) and treated with trifluoroacetic acid (6 mL). After 2 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 (2.08 g, quantitative yield based on 3 eq trifluoroacetic acid) as an orange oil. This material was dissolved in acetonitrile (0.33 mmol/mL) and used in the next step.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customAfter evaporating again from toluene
  3. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-b46ac37f6a2548f0bef7b478881c624c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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