HCID 54765598, compound → HCID 54767996, compound

HRID 1503278Notes

Reaction equation

HRID 1503278 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]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]>C(Cl)(Cl)Cl.CCO.[Pd]>[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]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 1

HCID 54765598HCID 54765598, compound

Product 1

HCID 54767996HCID 54767996, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid ethyl ester (7) was prepared as follows. Compound 6 (0.5 g) was dissolved in a mixture of CHCl3 (5 mL) and EtOH (15 mL). Palladium on carbon (10% wet, 0.25 g) was added to this solution, and shaken under hydrogen (50 PSI) for 24 hours at room temperature. After filtration over Celite, HCl (4N in 1,4-dioxane, 2 mL) was added to the mixture. The solvents were evaporated under vacuum to afford 2-amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid ethyl ester (7) as a white solid (0.4 g, 80%): 1H-NMR (400 MHz, CD3OD) δ: 7.75 (s, 1H), 7.65-7.71 (m, 2H), 7.35-7.51 (m, 4H), 7.05-7.15 (m, 5H), 4.2-4.4 (m, 3H), 3.4-3.5 (m, 2H), 1.2 (t, 3H, 7.2 Hz); LC/MS: m/z=401.5 [M+H]+ (Calc: 400.5).

Workup

  1. custom2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid ethyl ester (7) was prepared
  2. filtrationAfter filtration over Celite, HCl (4N in 1,4-dioxane, 2 mL)
  3. additionwas added to the mixture
  4. customThe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-89dcb0be0d2c4a2a8ae42b24b6583f92
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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