Water → HCID 58086725, compound

HRID 1261053Notes

Reaction equation

HRID 1261053 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:2]=1.[CH2:16]([NH:20][C:21]([N:23]1[C:31]2[C:26](=[C:27]([CH:32]=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)=[O:22])[CH2:17][CH2:18][CH3:19].[OH-].[K+].O>CO>[CH2:16]([NH:20][C:21]([N:23]1[C:31]2[C:26](=[C:27]([CH:32]([OH:33])[C:15]3[C:9]4[C:10](=[N:11][CH:12]=[C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[CH:8]=4)[NH:13][CH:14]=3)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridineHCID 58087441HCID 58087441, compound

Product 1

HCID 58086725HCID 58086725, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-Pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (89, 51 mg, 0.26 mmol, prepared as in Example 17) in methanol (2 mL), was added 4-Formyl-indole-1-carboxylic acid butylamide (519, 84 mg, 0.34 mmol) and potassium hydroxide (44 mg, 0.78 mmol). The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtrated and concentrated. The desired compound was isolated with silica gel column chromatography to give an off-white solid (520, 7 mg, 6%). MS (ESI) [M+H+]+=440.3.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5972ef818a8b45d9b9c49997c5f68fd2
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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