Dimethylformamide → HCID 86677597, compound

HRID 1397424Notes

Reaction equation

HRID 1397424 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[N:12]=2)=[CH:4][CH:3]=1.[CH3:22][N:23](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[N:12]=2)=[CH:4][CH:3]=1)#[N:23]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86677598HCID 86677598, compound

Product 1

HCID 86677597HCID 86677597, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
150 °C

Procedure

N-(2-(2-(4-Bromophenyl)oxazol-4-yl)ethyl)-2,2,2-trifluoroacetamide (200 mg, 0.55 mmol) was dissolved in dry DMF (10 mL) and the solution was purged with argon for 10 min. Zn(CN)2 (97 mg, 0.83 mmol) and PdCl2(dppf) (302 mg, 0.04 mmol) were added to the reaction mixture and heated to 150° C. for 48 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was diluted with water and the product was extracted with EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to get N-(2-(2-(4-cyanophenyl)oxazol-4-yl)ethyl)-2,2,2-trifluoroacetamide (150 mg), which was used for the next step without further purification. MS (ESI) m/z: Calculated for C14H10F3N3O2: 309.07. found: 307.9 (M−H)−.

Workup

  1. customthe solution was purged with argon for 10 min
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionthe product was extracted with EtOAc
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ad665179aaf4c8b853de302ba991a51
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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