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Potassium Cyanide → (s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

HRID 8279
Notes
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Reaction equation

HRID 8279 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26]OS(C)(=O)=O)[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C(OCC)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)=[N:14][N:13]3[C@H:23]([CH2:26][C:1]#[N:2])[CH2:24][CH2:25][C:12]=23)=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 9032Potassium CyanideHCID 87799512(S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester

Product 1

HCID 9902141(s)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-6-yl]-acetonitrile

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalyst
HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of potassium cyanide (44 mg, 0.67 mmol), tetrabutylammonium iodide (catalytic), and (S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester (54 mg, 0.135 mmol) in N,N-dimethylformamide (0.35 mL) and water (0.13 mL) is heated at 70° C. for 4 h. The mixture is cooled, taken up in ethyl acetate (20 mL), washed with water and brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (2% methanol/chloroform) to yield the title compound, 25 mg (56%).

Workup

  1. temperatureThe mixture is cooled
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (2% methanol/chloroform)

Sources & evidence

ORD record
ord-5b953fa7674c4f19b380bf9e67c072b5
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087626B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes