4-Methoxybenzylamine → HCID 86692458, compound

HRID 1748508Notes

Reaction equation

HRID 1748508 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1.Br[C:39]1[CH:40]=[CH:41][C:42]([C:45]2([C:51]#[N:52])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)=[N:43][CH:44]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:39]2[CH:40]=[CH:41][C:42]([C:45]3([C:51]#[N:52])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[N:43][CH:44]=2)=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 754524-MethoxybenzylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 67997680HCID 67997680, compound

Product 1

HCID 86692458HCID 86692458, compoundYield 21.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Palladium (II) acetate (90 mg), 2-(di-tert-butylphosphino)biphenyl (240 mg), sodium tert-butoxide (1.35 g), toluene (20 ml) and p-methoxybenzylamine (1.81 g) were added to 1-(5-bromopyridin-2-yl)cyclohexanecarbonitrile (2.5 g), and stirred at 100° C. for two hours. Water was added to the reaction solution, the resulting precipitate was filtered, the filtrate was extracted with ethyl acetate and the organic layer was concentrated. The residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-{5-[(4-methoxybenzyl)amino]pyridin-2-yl}cyclohexanecarbonitrile (650 mg) as a solid.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. extractionthe filtrate was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bfbbc6b4c3374b2a9a04a2b70cfc5ab9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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