Trifluoroacetic acid → 6'-Chloro-N,2-dimethyl-[3,4'-bipyridin]-3'-amine

HRID 347690Notes

Reaction equation

HRID 347690 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:10]=[N:11][C:12]([Cl:22])=[CH:13][C:14]=1[C:15]1[C:16]([CH3:21])=[N:17][CH:18]=[CH:19][CH:20]=1)C)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[Cl:22][C:12]1[N:11]=[CH:10][C:9]([NH:7][CH3:6])=[C:14]([C:15]2[C:16]([CH3:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58694607(6'-Chloro-2-methyl-[3,4']bipyridinyl-3'-yl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 586946066'-Chloro-N,2-dimethyl-[3,4'-bipyridin]-3'-amineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.14 g (0.42 mmol) (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-methyl-carbamic acid tert-butyl ester in 1.2 ml dichloromethane were added 0.40 ml (5.2 mmol) trifluoroacetic acid at room temperature. The reaction mixture was stirred at this temperature for 1.5 h. After addition of a 2 M aqueous sodium hydroxide solution the mixture was extracted with three portions of dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated. Flash chromatography gave 66 mg (68%) of the title compound.

Workup

  1. extractionwas extracted with three portions of dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bda1c21182e14d84b076a919219f96f8
Source dataset
uspto-grants-2007_02
Patent number
US07176205B2

Reaction notes

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