Dimethylformamide → HCID 86718466, compound

HRID 1396647Notes

Reaction equation

HRID 1396647 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[CH3:18][N:19](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:15]([C:5]1[CH:4]=[CH:3][C:2]([C:18]#[N:19])=[N:7][C:6]=1[O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([O-:17])=[O:16]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 61286363HCID 61286363, compound

Product 1

HCID 86718466HCID 86718466, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.2 g (4.6 mmol) of 6-chloro-3-nitro-2-(tetrahydro-pyran-4-yloxy)-pyridine, 550 mg (4.7 mmol) zinc cyanide, 260 mg (0.47 mmol) 1,1′-bis(diphenylphosphino)-ferrocene, 215 mg (0.24 mmol) Pd2dba3 in DMF are stirred at 120° C. for 5 h and 100° C. over night. After cooling to RT, the reaction mixture is diluted with EtOAc, washed with 10% aq. K2CO3 solution, water and brine, dried and evaporated. The residual is purified by FC, giving rise to 840 mg (73%) 5-Nitro-6-(tetrahydro-pyran-4-yloxy)-pyridine-2-carbonitrile.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with 10% aq. K2CO3 solution, water and brine
  3. customdried
  4. customevaporated
  5. customThe residual is purified by FC

Sources & evidence

ORD record
ord-edb53ec245aa4b6db1b5401a7cac8d85
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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