Iodine → 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-(4-morpholinyl)-

HRID 2114069Notes

Reaction equation

HRID 2114069 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[K+].[I:18]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:18][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[CH:8]=2)[NH:13][CH:14]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 598119225-(Morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 598119141H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-(4-morpholinyl)-Yield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 53 (0.096 g, 0.47 mmol) in DMF (2 mL) was added solid KOH (85%, 0.112 g, 1.69 mmol). After 20 min iodine (0.132 g, 0.52 mmol) was added in one portion. After stirring for 1 hour the mixture was cooled with ice-water bath, and water (10 mL) followed by saturated aqueous Na2S2O3 solution (2 mL) were added. The precipitate was filtered off, washed with water and dried to afford 54 (0.102 g, 66%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.11-3.15 (m, 4H), 3.85-3.89 (m, 4H), 7.19 (d, J=0.26 Hz, 1H), 7.33 (d, J=0.24 Hz, 1H), 8.08 (d, J=0.26 Hz, 1H), 9.81 (bs, 1H).

Workup

  1. temperaturewas cooled with ice-water bath
  2. additionwere added
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f3bd1f9874ca4af3baceb4f9168d68d1
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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