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

HRID 878171Notes

Reaction equation

HRID 878171 reaction equation
[F:1][CH:2]([F:36])[CH2:3][N:4]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[CH:31][C:30](F)=[CH:29][C:28]=1OC)C(=O)C1C=C(C(F)(F)F)N=C(C(F)(F)F)C=1.[CH3:37]C1C=CC=CC=1B(O)O>CCCCCCC.CCOC(C)=O>[F:36][CH:2]([F:1])[CH2:3][NH:4][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:37]

Participants

4

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 60198028HCID 60198028, compound2×

Product 1

HCID 86670770(2,2-Difluoro-ethyl)-(4-o-tolyl-pyridin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (2,2-difluoro-ethyl)-(4-iodo-pyridin-3-yl)-amine (example 153, intermediate b) 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. Colorless solid (93%). MS (ESI): m/z=248.1 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-427c2f2422254f098c62ede10b6bc5ba
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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