Acetic Acid → HCID 58316762, compound

HRID 1187281Notes

Reaction equation

HRID 1187281 reaction equation
[Cl:1][C:2]1[C:3]([NH2:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(O)(=O)C.C([BH3-])#N.[Na+].[CH:20]1([CH:23]=O)[CH2:22][CH2:21]1>C(O)C>[Cl:1][C:2]1[C:3]([NH:11][CH2:23][CH:20]2[CH2:22][CH2:21]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 260764515-Chloro-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 58316762HCID 58316762, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round bottom flask, 5-chloro-1H-pyrrolo[2,3-b]pyridin-4-ylamine (22, 0.21 g, 1.25 mmol) is combined with 3.5 mL of ethanol, acetic acid (0.38 g, 6.25 mmol), silica bound sodium cyanoborohydride (1.1 g, 1.02 mmol), and cyclopropanecarbaldehyde (23, 0.26 g, 4 mmol). The reaction mixture was stirred over night at room temperature, heated up to 145° C. until the reaction was complete, filtered, concentrated, and purified by flash chromatography to provide compound as a solid (24, 0.191 g; yield=69%).

Workup

  1. temperatureheated up to 145° C. until the reaction
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2388f06458044909afcd41a050baa81d
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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