Water → HCID 67260606, compound

HRID 2359055Notes

Reaction equation

HRID 2359055 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:7]([C:16]2[S:17][C:18](Br)=[CH:19][CH:20]=2)=[N:6]1)[CH:2]([CH3:4])[CH3:3].O.CO.C(O)=O.[CH3:28][N:29](C)C=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>[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:7]([C:16]2[S:17][C:18]([C:28]#[N:29])=[CH:19][CH:20]=2)=[N:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 18963719Formic acid methanolHCID 67260951HCID 67260951, compound

Product 1

HCID 67260606HCID 67260606, compoundYield 49%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a solution of 4-[1-isobutyl-3-(5-bromo-2-thienyl)-1H-pyrazol-4-yl]pyridine (1 eq, 0.28 mmol) in N,N-dimethylformamide (1 mL) were added zinc cyanide (0.5 eq, 0.14 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.2 eq, 0.055 mmol). The resulting mixture was stirred at 120° C. in the microwave for 10 min. Water was added and the aqueous layer was extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by preparative HPLC (SunFire 50×150 mm 5 μm, eau/methanol/formic acid) to afford 44 mg of 4-[1-isobutyl-3-(5-cyano-2-thienyl)-1H-pyrazol-4-yl]pyridine (49% yield).

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (SunFire 50×150 mm 5 μm

Sources & evidence

ORD record
ord-c62a221c81ae4c609c2b9a1425fbb3af
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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