2-Chlorophenylboronic acid → HCID 70663682, compound

HRID 878335Notes

Reaction equation

HRID 878335 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[O:11][CH:12]=[CH:13][N:14]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[O:11][CH:12]=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 70663320HCID 70663320, compound

Product 1

HCID 70663682HCID 70663682, compound

Procedure

The title compound was prepared in analogy to example 72, from 4-iodo-N-(oxazol-2-ylmethyl)pyridin-3-amine and 2-chlorophenylboronic 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), then EtOAc:MeOH (100:0 to 90:10). Light yellow solid (93%). MS (ESI): m/z=286.074 [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-b095580d89fd4296a6ac2d24abd5424d
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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