HCID 10354834, compound → HCID 10331769, compound

HRID 1376139Notes

Reaction equation

HRID 1376139 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:19])=O)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:19][CH2:17][C:9]1[NH:10][C:11]2[C:16]([C:8]=1[NH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 10354834HCID 10354834, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10331769HCID 10331769, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C. stir a solution of 3-(pyridin-4-ylamino)-1H-indole-2-carboxamide (1.26 g, 5 mmol) in THF (10 mL) and add dropwise a 1M solution of LAH in THF (25 mL, 25 mmol). Allow the reaction to warm to room temperature and then reflux overnight. Add aqueous 10% Rochelle salt solution, and extract the aqueous mixture with EtOAc. Concentrate the extract under vacuum and isolate 0.5 g of crude yellow solid. Purify the solid by preparative HPLC and obtain 0.2 g of the title compound as a solid: MS 239(M+H).

Workup

  1. customthe reaction
  2. temperaturereflux overnight
  3. extractionAdd aqueous 10% Rochelle salt solution, and extract the aqueous mixture with EtOAc
  4. concentrationConcentrate the
  5. extractionextract under vacuum
  6. customisolate 0.5 g of crude yellow solid
  7. customPurify the solid by preparative HPLC

Sources & evidence

ORD record
ord-217dd3c6a449491cad839fe88305f606
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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