Dimethylformamide → HCID 68849508, compound

HRID 1820956Notes

Reaction equation

HRID 1820956 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][C:10]([CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:11][C:12]=1[CH3:13])(=O)=O.[CH3:25][N:26](C=O)C>CCOC(C)=O.[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:25]([C:7]1[CH:8]=[CH:9][C:10]([CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:11][C:12]=1[CH3:13])#[N:26]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86623615HCID 86623615, compound

Product 1

HCID 68849508HCID 68849508, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 729 mg (1.97 mmol) of tert-butyl 3-(5-trifluoromethylsulfonyloxy-6-methylpyridin-2-yl)propanoate (from Step E) and 464 mg (3.95 mmol) of zinc cyanide in 10 mL of DMF was added 137 mg (0.12 mmol) of tetrakis(triphenylphosphine)palladium(0). After stirring at 85° C. for 4 h, the reaction mixture was diluted with 10 mL of EtOAc and filtered through a cake of Celite. Solid was washed with EtOAc (3×10 mL) and the filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 3:17 v/v EtOAc/hexanes as the eluant afforded 487 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.42 (s, 9H), 2.71 (d, J=7.4, 2H), 2.73 (s, 3H), 3.09 (d, J=7.3, 2H), 7.12 (d, J=8.0, 1H), 7.77 (d, J=8.0, 1H).

Workup

  1. filtrationfiltered through a cake of Celite
  2. washSolid was washed with EtOAc (3×10 mL)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4d42088b387244afaa6e819c1af668ad
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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