(4-Fluoro-2-methoxyphenyl)boronic acid → HCID 70663199, compound

HRID 878343Notes

Reaction equation

HRID 878343 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][O:12][CH2:11]1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([O:26][CH3:27])[CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][O:12][CH2:11]2)=[C:19]([O:26][CH3:27])[CH:18]=1

Participants

3

Reactant 2

HCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 70663281HCID 70663281, compound

Product 1

HCID 70663199HCID 70663199, compound

Procedure

The title compound was prepared in analogy to example 72, from 4-iodo-N-((tetrahydro-2H-pyran-3-yl)methyl)pyridin-3-amine and 4-fluoro-2-methoxyphenylboronic acid after a reaction time of 5 hours at reflux. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100) followed by EtOAc:MeOH (100:0 to 90:10). Yellow oil (106%). MS (ESI): m/z=317.166 [M+H]+.

Workup

  1. temperatureat reflux
  2. customThe compound was purified by silica gel chromatography on a 20 g column
  3. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-cac21441e8954839903402b1806ec725
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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