N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester → N-(3-Fluoropyridin-4-yl)-N-(3-methyl-1H-indol-1-yl)-2-aminoethanol

HRID 249249Notes

Reaction equation

HRID 249249 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[F:23])[N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[CH:8]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[N:6]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[CH:8]1)[CH2:5][CH2:4][OH:3]

Participants

4

Reactant 2

HCID 15818612N-(3-Fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 15818613N-(3-Fluoropyridin-4-yl)-N-(3-methyl-1H-indol-1-yl)-2-aminoethanolYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-(3-fluoro-4-pyridinyl)-N-(3-methyl-1H-indol-1-yl)glycine ethyl ester (5.0 g) in 100 ml of tetrahydrofuran cooled to ice bath temperature was added lithium aluminum hydride (1M solution in tetrahydrofuran, 30 ml) via syringe. The reaction was stirred for 0.5 hour. The mixture was quenched with NH4Cl and extracted three times with ethyl acetate. The organics were combined, washed with sat. NaCl and dried (MgSO4). After filtering, the solvent was evaporated to yield a solid (3.9 g) which was eluted with 50% ethyl acetate/dichloromethane on a silica gel column via high pressure liquid chromatography (HPLC). The desired fractions were evaporated to yield 3.7 g of a solid, m.p. 123°-125° C.

Workup

  1. customThe mixture was quenched with NH4Cl
  2. extractionextracted three times with ethyl acetate
  3. washwashed with sat. NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3c5048ecf797483eb9c0c81779708079
Source dataset
uspto-grants-1993_05
Patent number
US05214038

Reaction notes

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