Dimethylformamide → HCID 22943095, compound

HRID 412147Notes

Reaction equation

HRID 412147 reaction equation
FC(F)(F)S(OC1[C:12]([Cl:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[Cl:15])(=O)=O.CCO[C:21]([CH3:23])=O.C[N:25](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>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]#[N:25])[CH:9]=[C:8]([Cl:15])[C:21]=1[CH3:23]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 18536033HCID 18536033, compound

Product 1

HCID 22943095HCID 22943095, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 178418397HCID 178418397, compoundCatalyst2×

Conditions

Temperature
80 °C

Procedure

To a degassed solution of the triflate from Step A (40.92 g, 132.8 mmol) in 250 mL of DMF was added Zn(CN)2 (15.6 g, 132.8 mmol) and Pd(PPh3)4 (7.67 g, 6.64 mmol). The reaction was stirred at 80° C. for three days. Another portion of Zn(CN)2 (10 g) and Pd(PPh3)4 (5 g) was added the reaction was stirred at 80° C. for 24 hours, then cooled to room temperature. The solution was poured into EtOAc, washed with water, sat. aq. NaHCO3, and brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by crystallization (10% EtOAc/hexane) provided the titled product as white needles.

Workup

  1. stirringwas stirred at 80° C. for 24 hours
  2. temperaturecooled to room temperature
  3. washwashed with water, sat. aq. NaHCO3, and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude product
  8. customPurification
  9. customby crystallization (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-b7c12ef7bea3465192ff70c67dfcc6d6
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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