HCID 54765933, compound → HCID 54765934, compound

HRID 1503285Notes

Reaction equation

HRID 1503285 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([N+:29]([O-])=O)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[CH:8]=1)[CH3:2]>[Pd].C(Cl)(Cl)Cl.CCO>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([NH2:29])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:20][CH:21]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 54765933HCID 54765933, compound

Product 1

HCID 54765934HCID 54765934, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

2-Amino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid ethyl ester (33) was prepared as follows: Palladium on carbon (10% wet, 0.4 g) was added to a solution of compound 32 (1.2 g) in CHCl3 (10 mL) and EtOH (30 mL). The reaction mixture was shaken under hydrogen (50 PSI) for 24 hours at room temperature. After filtration on Celite, HCl (4N in 1,4-dioxane, 4 mL) was added and the solvents were evaporated under vacuum to give compound 33 as a blue solid (1.1 g, 90%): LC/MS: m/z=401.1 [M+H]+ (Calc: 400.5).

Workup

  1. custom2-Amino-3-[1-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid ethyl ester (33) was prepared
  2. filtrationAfter filtration on Celite, HCl (4N in 1,4-dioxane, 4 mL)
  3. additionwas added
  4. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-70a7eeedbdd34a0f90877da66d6c8965
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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