Potassium Carbonate → HCID 86690800, compound

HRID 1471762Notes

Reaction equation

HRID 1471762 reaction equation
Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH:19]([O:27][CH3:28])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[OH:26]>CC#N>[CH3:28][O:27][CH:19]([O:18][CH3:17])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[O:26][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219277766-(Bromomethyl)pyridine-3-carbonitrileHCID 86690788HCID 86690788, compound

Product 1

HCID 86690800HCID 86690800, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 6-(bromomethyl)pyridine-3-carbonitrile (3 g, 15.23 mmol, 1.00 equiv) in CH3CN (100 mL). Potassium carbonate (4.24 g, 30.68 mmol, 2.00 equiv) and 4-(dimethoxymethyl)pyridin-3-ol (2.83 g, 16.73 mmol, 1.10 equiv) were added to the reaction mixture. The resulting solution was stirred for 2 h at 50° C., and then it was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3) as eluent to furnish 1.4 g (32%) of 6-([[4-(dimethoxymethyl)pyridin-3-yl]oxy]methyl)pyridine-3-carbonitrile as a red solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationit was concentrated under vacuum

Sources & evidence

ORD record
ord-c29c16fe57ce4ce0b439651bb1c4425b
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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