(2-Aminophenyl)boronic acid → HCID 86670806, compound

HRID 878255Notes

Reaction equation

HRID 878255 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>>[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1

Participants

3

Reactant 2

HCID 2773216(2-Aminophenyl)boronic acidHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670806HCID 86670806, compound

Procedure

The title compound was prepared in analogy to example 72, from N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide (example 98, intermediate a) and 2-amino-phenylboronic acid after a reaction time of 4 hours. The compound was purified by silica gel chromatography on a 50 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Further purification by preparative HPLC (Gemini NX) with a gradient of MeOH:water (containing 0.05% formic acid) (80:20 to 98:2). Colorless solid (19%). MS (ESI): m/z=440.119 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 50 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  3. customFurther purification by preparative HPLC (Gemini NX) with a gradient of MeOH

Sources & evidence

ORD record
ord-b4707118036f43c794c8ec6233d5e63d
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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