Sodium Cyanide → HCID 19916787, compound

HRID 1756109Notes

Reaction equation

HRID 1756109 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1.[C-]#N.[Na+].C[N:16]([CH2:18][C:19]1C2C(=NC=C(F)C=2)NC=1C)C>O>[C:18]([CH2:19][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[NH:8][C:9]=1[CH3:11])#[N:16]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 199167765-Fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridineHCID 21743840HCID 21743840, compound

Product 1

HCID 19916787HCID 19916787, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Mannich reagent (0.8 ml, prepared according to Liebigs (1971) Ann. Chem., 743, 95-111) was added under stirring to pre-cooled (-78° C.) 5-fluoro-2-methylpyrrolo[2,3-b]pyridine (0.33 g, 2.2 mmol) under argon. The flask containing the reaction mixture was then placed in an ice bath and stirring was continued to give a white suspension. The ice lumps melted within 2 h and the resulting water bath was allowed attain room temperature. After 24 h almost all suspension had dissolved. The reaction mixture was cooled in an ice bath, diluted with deinionized water (8 ml) and extracted with diethyl ether (2×5 ml) to remove some remaining starting material and a by-product (propably the corresponding Mannich dimer). Sodium cyanide (1.08 g, 0.022 mol) was added to the water phase, assumed to contain 3-(dimethylaminomethyl)-5-fluoro-2-methylpyrrolo[2,3 -b]pyridine, and the resulting solution was refluxed for 2 h to afford a suspension which was isolated by filtration. Purification by flash chromatography (SiO 2 /CH2Cl2 :MeOH 19:1) gave 0.28 g (67%, two steps) of 3-(cyanomethyl)-5-fluoro-2-methylpyrrolo[2,3-b]pyridine.

Workup

  1. additionThe flask containing the reaction mixture
  2. customwas then placed in an ice bath
  3. stirringstirring
  4. customto give a white suspension
  5. customwas allowed attain room temperature
  6. dissolutionAfter 24 h almost all suspension had dissolved
  7. temperatureThe reaction mixture was cooled in an ice bath
  8. extractionextracted with diethyl ether (2×5 ml)
  9. customto remove
  10. temperaturethe resulting solution was refluxed for 2 h
  11. customto afford a suspension which
  12. customwas isolated by filtration
  13. customPurification by flash chromatography (SiO 2 /CH2Cl2 :MeOH 19:1)

Sources & evidence

ORD record
ord-c5e01f1b9fd84255901d63a978e277c1
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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