Potassium Iodide → HCID 18510478, compound

HRID 1370184Notes

Reaction equation

HRID 1370184 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1.[I-].[K+].[H-].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:4]1[C:5]2=[CH:6][C:7]3[CH:12]=[CH:11][CH:10]=[N:9][C:8]=3[N:13]2[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 17817560HCID 17817560, compound

Product 1

HCID 18510478HCID 18510478, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(3-Chloro-propyl)-1H-pyrrolo[2,3-b]pyridine (5.6 g) was dissolved in acetonitrile under a stream of argon. Potassium iodide (6 g) was added, and sodium hydride in mineral oil (4.60 g) added in small portions. After stirring 2 h at room temperature, the mixture was poured onto a mixture of ice and saturated sodium hydrogencarbonate solution. The organics were extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated to afford 2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene as a crude pale brown solid (4.5 g, 99%), which was used without further purification. MS (EI) 159 (M+H)+, 143, 100; 1H NMR (δ, CDCl3) 8.19 (dd,1H, J=1,5 Hz), 7.80 (dd,1H, J=1,8 Hz), 6.99 (dd,1H, J=5,8 Hz), 6.12 (s,1H), 4.22 (t,2H, J=6 Hz), 3.05 (t,2H, J=8 Hz), 2.63 (dt,2H, J=6,8 Hz) ppm.

Workup

  1. extractionThe organics were extracted twice with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-420df9f574074d09864cb327fc7f7f47
Source dataset
uspto-grants-2003_06
Patent number
US06583134B2

Reaction notes

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