Diisopropylethylamine → n-[2-(3-Chloro-5-trifluoromethyl-pyridin-2-yl) ethyl]-2-trifluoromethyl-nicotinamide

HRID 2354936Notes

Reaction equation

HRID 2354936 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[Cl:14][C:15]1[C:16]([CH2:25][CH2:26][NH2:27])=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:14][C:15]1[C:16]([CH2:25][CH2:26][NH:27][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[N:11][C:3]=2[C:2]([F:1])([F:13])[F:12])=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 27775472-(Trifluoromethyl)pyridine-3-carboxylic acidHCID 119619683-Chloro-5-(trifluoromethyl)-2-pyridineethanamine

Product 1

HCID 11741540n-[2-(3-Chloro-5-trifluoromethyl-pyridin-2-yl) ethyl]-2-trifluoromethyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 204 mg (1 mmol) of 2-trifluormethyl nicotinic acid, 200 mg (0.9 mmol) of 2-(3-chloro-5-trifluormethyl-pyridin-2-yl)-ethylamine and 620 mg (1.3 mmol) of bromotripyrrolidinophosphonium hexafluorophosphate and 230 mg (1.8 mmol) N,N-Diisopropylethylamine in 8 ml methylene chloride is stirred for 20 h at room temperature.

Sources & evidence

ORD record
ord-b9119123c97c4878931e45b996798e7a
Source dataset
uspto-grants-2010_07
Patent number
US07754741B2

Reaction notes

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