3-Fluoro-5-(trifluoromethyl)benzoyl chloride → HCID 70663278, compound

HRID 878133Notes

Reaction equation

HRID 878133 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:22](Cl)=[O:23]>>[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:22]([N:14]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:16][CH3:17])[CH3:15])=[O:23]

Participants

3

Reactant 2

HCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 70663207[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 70663278HCID 70663278, compound

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine and 3-fluoro-5-(trifluoromethyl)benzoic acid chloride (CAS RN 171243-30-4). The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product-containing fractions were pooled and evaporated. The yellow solid was further purified by preparative HPLC (Phenomenex Gemini® column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (50:50 to 95:5). Light yellow solid (23%). MS (ESI): m/z=423.113 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  3. customevaporated
  4. customThe yellow solid was further purified by preparative HPLC (Phenomenex Gemini® column) with a gradient of acetonitrile

Sources & evidence

ORD record
ord-c27d37285c2847288f598beb07e1c90a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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