Ethyl Acetate → HCID 10331818, compound

HRID 1376137Notes

Reaction equation

HRID 1376137 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[N:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:4][OH:3])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 104689203-(4-Pyridinylamino)-1H-indole-2-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 10331818HCID 10331818, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

At 0° C. stir a solution of 3-(pyridin-4-ylamino)-1H-indole-2-carboxylic acid ethyl ester (1.4 g, 5 mmol) in THF (15 mL) and add a 1M solution of LAH in THF (8 mL, 8 mmol). Allow the reaction to warm to room temperature and stir for an additional 0.5 h. Add aqueous NH4Cl solution, ethyl acetate and brine. Filter the solid that forms in the biphasic mixture to obtain 0.56 g (47%) of the title compound as a beige solid: MS 240(M+H); HPLC: Rt=1.04 min; TLC (silica gel, dichloromethane/MeOH, 4:1), Rf=0.6.

Workup

  1. customthe reaction
  2. filtrationFilter the solid that forms in the biphasic mixture

Sources & evidence

ORD record
ord-70ae0cd02ab84d4382b57eb620ba838f
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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