Pyridine → 3-bromo-N-[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]benzamide

HRID 539809Notes

Reaction equation

HRID 539809 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[N:16]([CH:17]=2)[N:15]=[C:14]([C:18]2[C:19]([C:24]([F:27])([F:26])[F:25])=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=[CH:12]3)=[CH:5][C:3]=1[NH2:4].[Br:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33].N1C=CC=CC=1>CC#N>[Br:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([NH:4][C:3]1[CH:5]=[C:6]([C:9]2[N:10]=[C:11]3[N:16]([CH:17]=2)[N:15]=[C:14]([C:18]2[C:19]([C:24]([F:25])([F:27])[F:26])=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=[CH:12]3)[CH:7]=[CH:8][C:2]=1[CH3:1])=[O:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74377Benzoyl chloride, 3-bromo-HCID 680893232-Methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]aniline

Product 1

HCID 680892223-bromo-N-[2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 20 mL vial is charged with 2-methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]aniline (0.444 g, 1.2 mmol), 3-bromobenzoyl chloride (0.378 mL, 1.8 mol), pyridine (0.292 mL, 3.6 mmol), MeCN (4 mL) and the mixture is stirred at room temperature for 18 hr. The reaction mixture is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in CH2Cl2) to give the title compound (530 mg). LCMS (m/z)=552.3 and 554.3 [M+H]+, tR=3.04 min.

Workup

  1. concentrationThe reaction mixture is concentrated onto celite
  2. custompurified by silica gel chromatography (0-100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-96d41f39610c45af88ca531c4d11ad9c
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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