2-Methylphenyl boronic acid → (4-o-Tolyl-pyridin-3-yl)-(2,2,2-trifluoro-ethyl)-amine

HRID 878158Notes

Reaction equation

HRID 878158 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([F:13])([F:12])[F:11].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O>CCCCCCC.CCOC(C)=O>[C:15]1([CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([F:13])([F:12])[F:11]

Participants

4

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 706635143-Pyridinamine, 4-iodo-N-(2,2,2-trifluoroethyl)-

Product 1

HCID 70663500(4-o-Tolyl-pyridin-3-yl)-(2,2,2-trifluoro-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-(2,2,2-trifluoro-ethyl)-amine and 2-methylphenylboronic acid (CAS RN 16419-60-6) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light brown solid (91%). MS (ESI): m/z=267.11 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-0b23271aa79b4fc8a4db2f2e134fa8d0
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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