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Water → HCID 67147578, compound

HRID 490429
Notes
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Reaction equation

HRID 490429 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][CH3:12])(=[O:10])[CH:8]=[CH2:9].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[NH:20][CH:19]=[C:18]2[C:26]1[N:34]([S:35]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)(=[O:37])=[O:36])[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[CH:27]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]([CH2:9][CH2:8][C:7]([O:11][CH3:12])=[O:10])[CH:19]=[C:18]2[C:26]1[N:34]([S:35]([C:38]2[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][CH:43]=2)(=[O:37])=[O:36])[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 22477225HCID 22477225, compound

Product 1

HCID 67147578HCID 67147578, compound

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

0.34 g of potassium carbonate and 0.243 ml of methyl acrylate are added, dropwise, to a solution of 1 g of 2-(5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine in 20 ml of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20° C. The reaction medium is agitated at the same temperature for 16 hours. 20 ml of water and 20 ml of ethyl acetate are added. After separation by settling out, the organic phase is dried over sodium sulfate, filtered, and then concentrated under reduced pressure. After purification by flash chromatography (silica, dichloromethane as eluent, argon), the fractions containing the product are concentrated under reduced pressure. 1 g of methyl 3-{5,6-dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]indol-1-yl}propionate is thus obtained, the characteristics of which are as follows:

Workup

  1. customin the region of 20° C
  2. customAfter separation
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by flash chromatography (silica, dichloromethane as eluent, argon)
  7. additionthe fractions containing the product
  8. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a287ef6bb1648308a0371853c7dcc7d
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes