Methanol → HCID 86687911, compound

HRID 1400064Notes

Reaction equation

HRID 1400064 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[CH2:17][C:18]#[N:19])[CH:5]=[CH:4][N:3]=1.CO>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[CH2:17][C:18]#[N:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 86687910HCID 86687910, compound

Product 1

HCID 86687911HCID 86687911, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(2-((2-Chloropyrimidin-4-yl)ethynyl)-5-fluorophenyl)acetonitrile (0.695 g, 2.56 mmol) is dissolved in ethyl acetate (90 ml), and 10% Pd/C (0.142 g, 0.133 mmol) are added. The suspension is hydrogenated at RT for 24 h under an H2 pressure of 40 psi in a Parr apparatus (hydrogenation apparatus). Since the reaction proceeds very sluggishly, 9 ml of methanol and further catalyst are added (10% Pd/C (0.142 g, 0.133 mmol). Over a further 28 h, 142 mg of catalyst are added three further times until complete conversion is observed. The dark suspension is filtered, washed with ethyl acetate and methanol, and the filtrate is evaporated to dryness in vacuo. Chromatography of the 700 mg of crude product on silica gel with petroleum ether/ethyl acetate=7:3 gives 386 mg of 2-(2-(2-(2-chloropyrimidin-4-yl)ethyl)-5-fluorophenyl)acetonitrile (1.400 mmol, 54.7% yield) as yellowish oil;

Workup

  1. waitOver a further 28 h
  2. filtrationThe dark suspension is filtered
  3. washwashed with ethyl acetate and methanol
  4. customthe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d0c46a27c47148dca81ea52e0f2ab44a
Source dataset
uspto-grants-2014_12
Patent number
US08906916B2

Reaction notes

Loading…