Ammonia → HCID 23130740, compound

HRID 2080155Notes

Reaction equation

HRID 2080155 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[S:13][C:14](Br)=[CH:15][CH:16]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.N.[CH3:19][N:20]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.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>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:11])[C:12]3[S:13][C:14]([C:19]#[N:20])=[CH:15][CH:16]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 23130438HCID 23130438, compound

Product 1

HCID 23130740HCID 23130740, compoundYield 58%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a solution of benzofuran-5-yl-(5-bromo-thiophen-2-yl)-methanol described in Preparation Example 176 (755 mg, 2.44 mmol) in 1-methyl-2-pyrrolidinone (15 mL) were added zinc cyanide (344 mg, 2.93 mmol) and tetrakis(triphenylphosphine)palladium (282 mg, 0.244 mmol), and the mixture was stirred at 120° C. for 3 hours. The reaction mixture was cooled to room temperature, then, aqueous ammonia was added, and the solution was filtered through Celite pad. The mother liquor was extracted with ethyl acetate, and the organic layer was washed with brine. Anhydrous magnesium sulfate was added to the organic layer for drying, which was then filtered, the filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=3/1), and the title compound (364 mg, 58%) was obtained as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solution was filtered through Celite pad
  3. extractionThe mother liquor was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. additionAnhydrous magnesium sulfate was added to the organic layer
  6. customfor drying
  7. filtrationwhich was then filtered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-1df75d2270e249c2ad5dcf0632236fc0
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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