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

HRID 347683Notes

Reaction equation

HRID 347683 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'-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the obtained (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-methyl-carbamic acid tert-butyl ester in dichloromethane is added 0.40 ml trifluoroacetic acid at room temperature. The reaction mixture is stirred at this temperature for about 1.5 h. After addition of an aqueous sodium hydroxide solution, the mixture is extracted with dichloromethane. The combined organic layers are dried and concentrated to give the compound (6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-methyl-amine of formula IX.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. customThe combined organic layers are dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8995d8fb83f54db895af2038a0dde5f0
Source dataset
uspto-grants-2007_02
Patent number
US07176205B2

Reaction notes

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