HCID 66696723, compound → HCID 2739747, compound

HRID 1672590Notes

Reaction equation

HRID 1672590 reaction equation
Br[C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[C:17]([Zn]C#N)#[N:18]>CN(C=O)C.O.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>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([C:6]2[O:5][CH:4]=[N:3][C:2]=2[C:17]#[N:18])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 66696723HCID 66696723, compoundHCID 178514179HCID 178514179, compound2×

Product 1

HCID 2739747HCID 2739747, compoundYield 240.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of Example 56B (500 mg, 1.71 mmol), dicyanozinc (221 mg, 1.88 mmol), and Pd(Ph3P)4 (101 mg, 0.087 mmol) in DMF (3 mL) was heated in a microwave reactor to 160° C. for 6 min. The reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with EtOAc. The combined organic extracts were filtered through celite, and the filtrate was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. An identical reaction was then performed using Example 56B (1.0 g, 3.4 mmol), dicyanozinc (442 mg, 3.77 mmol), and Pd(Ph3P)4 (198 mg, 0.171 mmol) in DMF (6 mL). The crude product from both reactions was combined and purified by chromatography on silica gel (25% EtOAc/hexanes) to afford 980 mg (80%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.10 (dd, J=8.9, 0.7, 2H), 8.00 (s, 1H), 7.81 (dd, J=8.7, 0.5, 2H). MS (DCI+) m/z 256 (M+NH4).

Workup

  1. extractionextracted with EtOAc
  2. filtrationThe combined organic extracts were filtered through celite
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customAn identical reaction
  8. custompurified by chromatography on silica gel (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-960eab0d280c48bebd8849746f1d77cd
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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