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

HRID 878183Notes

Reaction equation

HRID 878183 reaction equation
F[C:2]1[C:7](F)=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])C(=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=[C:4](OC)[CH:3]=1.[CH3:40]C1C=CC=CC=1B(O)O>C(Cl)Cl.CO>[CH3:37][S:34]([CH2:33][CH2:32][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH3:40])(=[O:35])=[O:36]

Participants

4

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663340(2-Methanesulfonyl-ethyl)-(4-o-tolyl-pyridin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-(2-methanesulfonyl-ethyl)-amine (example 158, intermediate b) and 2-methylphenylboronic acid (CAS RN 16419-60-6) and using a gradient of CH2Cl2: methanol (100:0 to 85:15) for the chromatographic purification. Brown oil (85%). MS (ESI): m/z=291.12 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-41fd97792f0a40d494bc08a049cbb5b9
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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