Potassium Iodide → HCID 10292075, compound

HRID 1835180Notes

Reaction equation

HRID 1835180 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:7][C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH2:20][CH2:21][NH:22]C(=O)C)[CH:11]=3)=[CH:9][C:2]=12.N1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(CC)=O>[N:22]1([CH2:21][CH2:20][CH2:19][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:8]3[NH:7][C:3]4=[N:4][CH:5]=[CH:6][N:1]=[C:2]4[CH:9]=3)=[CH:11]2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 9923710HCID 9923710, compound

Product 1

HCID 10292075HCID 10292075, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-indol-1-yl]-propylbromide [250 mg, Reference Example 4], morpholine (0.5 mL), potassium carbonate (100 mg) and potassium iodide (2 crystals) in ethyl methyl ketone was heated at reflux for 2 hours. The mixture was then allowed to cool to ambient temperature over 16 hours then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1, v/v) to give a yellow glass which was triturated with ethyl acetate and pentane to give the title compound (40 mg) as a yellow solid, m.p. 180-185° C. MS: 362 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customthen evaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1
  5. customv/v) to give a yellow glass which
  6. customwas triturated with ethyl acetate and pentane

Sources & evidence

ORD record
ord-5a0be2bdec0547f8b4572b28819f4513
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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