Tetramethyltin → 5,6-Dimethoxy-3-methyl-2-pyridinecarbonitrile

HRID 595046Notes

Reaction equation

HRID 595046 reaction equation
Cl[C:2]1[C:3]([C:12]#[N:13])=[N:4][C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[Cl-].[Li+].[CH3:16][Sn](C)(C)C>CN(C=O)C.[Cl-].[NH4+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH3:16])[C:3]([C:12]#[N:13])=[N:4][C:5]=1[O:10][CH3:11]

Participants

7

Reactant 3

HCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 73554910HCID 73554910, compound

Product 1

HCID 895353615,6-Dimethoxy-3-methyl-2-pyridinecarbonitrile

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-5,6-dimethoxypyridine-2-carbonitrile (1-6d, 1 g, 5.04 mmol) in DMF (20 mL) was added lithium chloride (2.1 g, 50.4 mmol), Pd(PPh3)4 (1.16 g, 1.0 mmol) and tetramethyltin (4.5 g, 25.2 mmol). The resulting mixture was heated at 100° C. overnight, cooled to rt, diluted with saturated ammonium chloride and extracted with EtOAc. The combined organic layers were dried and concentrated to give a yellow oil which was purified by column chromatography (SiO2, 80 g, 0-30% EtOAc in hexane) to give 1-6e as a bone powder. ESI+ MS [M+H]+ C9H11N2O2=179.1.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customto give a yellow oil which
  6. customwas purified by column chromatography (SiO2, 80 g, 0-30% EtOAc in hexane)
  7. customto give 1-6e as a bone powder

Sources & evidence

ORD record
ord-2449b7c5942a44e5b0406b44ccd2f62e
Source dataset
uspto-grants-2016_01
Patent number
US09242995B2

Reaction notes

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