Water → HCID 14495336, compound

HRID 1421761Notes

Reaction equation

HRID 1421761 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=1.O.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:22]#[N:23])[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 53919960HCID 53919960, compound

Product 1

HCID 14495336HCID 14495336, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

4-Cyano-3-(trifluoromethanesulfonyloxy)-benzoic acid methyl ester (from L-819,063 step 1, 4.92 g, 16 mmol) was dissolved in DMF (22.9 ml) and treated with Zn(CN)2 (1.3 g, 11.2 mmol). The reaction mixture was degassed by bubbling in argon for 1 hr. Pd(PPh3)4 (924 mg, 0.8 mmol) was then added and the reaction was heated to 100° C. for 15 hours. The reaction mixture was poured into water (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (100% CH2Cl2) to yield the desired compound.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling in argon for 1 hr
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe organic layer was washed with water (2×10 mL), 5% HCl (1×10 mL), brine (1×10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-d008dd91d4f145f89cedefddeaac6f7b
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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