Cyanide → HCID 57833595, compound

HRID 730069Notes

Reaction equation

HRID 730069 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].[C-:37]#[N:38]>[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.CN(C)C=O>[F:36][C:2]([F:35])([F:1])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:37]#[N:38])[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4]

Participants

7

Reactant 2

HCID 5975CyanideHCID 57833591HCID 57833591, compound

Product 1

HCID 57833595HCID 57833595, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23938PalladiumCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of trifluoromethanesulfonic acid 9-[8-(2,2, 2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-4-yl ester in a deoxygenated solvent such as dimethyl formamide (0.5 to 2 M solution) may be treated with a catalytic amount of a palladium catalyst such as tetrakis(triphenylphosphine) palladium ( 0.01 to 0.1 equiv) and a cyanide source such as zinc cyanide (1.5 to 3 equiv). The mixture may be heated to 100° C. to 150° C. under an argon atmosphere for 1 to 5 hr. After cooling, the mixture may be partitioned between a saturated sodium bicarbonate solution and an organic solvent such as ethyl acetate. The organic phase may be separated, dried over an appropriate drying agent such as sodium sulfate, filtered, and evaporated. The residue may be purified over silica gel using a mixture of organic solvents or via reverse phase chromatography to yield Compound 2b.

Workup

  1. temperatureThe mixture may be heated to 100° C. to 150° C. under an argon atmosphere for 1 to 5 hr
  2. temperatureAfter cooling
  3. customthe mixture may be partitioned between a saturated sodium bicarbonate solution
  4. customThe organic phase may be separated
  5. dry with materialdried over an appropriate drying agent such as sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue may be purified over silica gel using
  9. additiona mixture of organic solvents

Sources & evidence

ORD record
ord-b8fac990b34e4118b4b18deebfbc8184
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

Loading…