Water → HCID 67147475, compound

HRID 490478Notes

Reaction equation

HRID 490478 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:27][CH3:28])=[C:20]([O:23][CH2:24][CH2:25]I)[CH:21]=2)[C:16]([C:29]2[N:37]([S:38]([C:41]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[C:32]3=[N:33][CH:34]=[CH:35][CH:36]=[C:31]3[CH:30]=2)=[CH:15]1.O>C(#N)C.C(OCC)(=O)C>[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:27][CH3:28])=[C:20]([O:23][CH2:24][CH2:25][N:7]3[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)[CH:21]=2)[C:16]([C:29]2[N:37]([S:38]([C:41]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[C:32]3=[N:33][CH:34]=[CH:35][CH:36]=[C:31]3[CH:30]=2)=[CH:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67147570HCID 67147570, compound

Product 1

HCID 67147475HCID 67147475, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

0.11 g of potassium carbonate and 0.14 ml of morpholine are added to a solution of 0.24 g of 2-[1-methyl-5-methoxy-6-(2-iodoethoxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 24 ml of acetonitrile, under an inert argon atmosphere at a temperature in the region of 20° C. The reaction medium is heated at 60° C. for 24 hours. After cooling, the reaction medium is concentrated under reduced pressure. The oil obtained is taken up with 10 ml of water and 10 ml of ethyl acetate. After separation by settling out, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, 30/70 by volume ethyl acetate/cyclohexane as eluents). The fractions containing the product are concentrated under reduced pressure. 0.24 g of 2-[1-methyl-5-methoxy-6-(2-morpholin-4-ylethoxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is thus obtained, the characteristics of which are as follows:

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction medium is concentrated under reduced pressure
  3. customThe oil obtained
  4. customAfter separation
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customis purified by flash-pack chromatography (silica, 30/70 by volume ethyl acetate/cyclohexane as eluents)
  10. additionThe fractions containing the product
  11. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf271645907140baa2badc404506e2d3
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

Loading…