Diisopropylethylamine → N'-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)acetohydrazide

HRID 1867898Notes

Reaction equation

HRID 1867898 reaction equation
[Br:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH3:17][C:18]1[C:23]([CH2:24][C:25](O)=[O:26])=[CH:22][CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[N:19]=1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.BrC1C(C2C=CC(Cl)=CC=2)=CC(NNC(=O)CC2C=NC(C(F)(F)F)=CC=2)=NC=1>CC#N>[Br:1][C:2]1[C:3]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[CH:4][C:5]([NH:8][NH:9][C:25](=[O:26])[CH2:24][C:23]2[C:18]([CH3:17])=[N:19][C:20]([C:28]([F:29])([F:31])[F:30])=[CH:21][CH:22]=2)=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 115575962-(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)acetic acidHCID 57979738N'-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetohydrazideHCID 579797505-Bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine

Product 1

HCID 57979751N'-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)acetohydrazideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (160 mg, 97%) as a beige powder was prepared from 5-bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine (100 mg, 0.33 mmol), 2-(2-methyl -6-(trifluoromethyl)pyridin-3-yl)acetic acid (75 mg, 0.33 mmol), (i-Pr)2EtN (86 mg, 0.66 mmol) and bromotripyrrolidinophosphonium hexafluorophosphate (PyBop, 190 mg, 0.37 mmol) in CH3CN (2.5 mL) by the procedures analogous to those described for N′-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetohydrazide (Example 56C). LC/MS (method B): retention time=1.92 min, [M+H]+=499.0.

Sources & evidence

ORD record
ord-14b78fcfab244c91b8392cb36217ab5f
Source dataset
uspto-grants-2009_12
Patent number
US07632837B2

Reaction notes

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