Trifluoroacetic acid → 2-(3-(Bromo(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate

HRID 1666476Notes

Reaction equation

HRID 1666476 reaction equation
[Br:1][C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH:17]=1)=[C:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[Br:1][C:2](=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876318Tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

Product 1

HCID 866239102-(3-(Bromo(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetateYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (0.42 g, 0.82 mmol) in CH2Cl2 (10 mL) was added TFA (3 mL). The pale yellow solution went to a darker yellow solution. The reaction was stirred at room temperature for 5 h. The reaction was concentrated to give the title compound as a solid (235 mg, 54% yield).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-90cc301817a3410485d49bae5d1efd67
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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