Dimethylformamide → HCID 178469849, compound

HRID 1820973Notes

Reaction equation

HRID 1820973 reaction equation
[OH:1][C:2]1[C:12](I)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH3:14][N:15](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[C:14]([C:12]1[C:2]([OH:1])=[N:3][CH:4]=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178469850Ethyl 6-hydroxy-5-iodonicotinate

Product 1

HCID 178469849HCID 178469849, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 716 mg (2.44 mmol) of ethyl 6-hydroxy-5-iodonicotinate and 573 mg (4.88 mmol) of zinc cyanide in 10 mL of DMF was added 169 mg (0.15 mmol) of tetrakis(triphenylphosphine)palladium(0). After stirring at 80° C. overnight, the mixture was filtered through a cake of Celite. The filtrate was washed with brine (10 mL), H2O (3×10 mL), and brine (10 μL), dried over MgSO4, and concentrated. Chromatography on a Biotage 40M cartridge using 4:1 v/v EtOAc/hexanes as the eluant gave 222 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.29 (d, J=7.1, 3H), 4.28 (q, J=7.1, 2H), 8.31 (d, J=2.5, 1H), 8.42 (d, J=2.8, 1H).

Workup

  1. filtrationthe mixture was filtered through a cake of Celite
  2. washThe filtrate was washed with brine (10 mL), H2O (3×10 mL), and brine (10 μL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8fdce404eb8845c6be9cd42e04c0d84a
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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