Acetonitrile → 2-Amino-3-(5-(5-phenylthiophen-2-yl)-1H-indol-3-yl)propanoic acid

HRID 419270

Reaction equation

HRID 419270 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[NH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:17]1([C:23]2[S:27][C:26](B(O)O)=[CH:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].C(#N)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][CH:2]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:26]3[S:27][C:23]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:24][CH:25]=3)[CH:14]=2)[NH:9][CH:8]=1)[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 967355-Bromo-DL-tryptophanHCID 2776315(5-Phenylthiophen-2-yl)boronic acid

Product 1

HCID 236333272-Amino-3-(5-(5-phenylthiophen-2-yl)-1H-indol-3-yl)propanoic acidYield 19.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

2-Amino-3-(5-bromo-1H-indol-3-yl)-propionic acid (0.020 g, 0.071 mmol) was added to a 5 ml microwave vial, which contained 5-phenyl-thiophen-2-boronic acid (0.016 g, 0.078 mmol), Na2CO3 (0.015 g, 0.142 mmol), acetonitrile (1.5 ml)/water (1.5 ml) and dichlorobis(triphenylphosphine)-palladium (3 mg, 0.003 mmol). Microwave vial was capped and stirred at 150° C. for 5 min under microwave radiation. Reaction mixture was cooled, filtered through a syringe filter and then separated by a reverse phase preparative-HPLC using YMC-Pack ODS 100×30 mm ID column (MeOH/H2O/TFA solvent system). The pure fractions were concentrated in vacuum. The product was then suspended in 5 ml of water, frozen and lyophilized to give 5 mg of pure product, 2-amino-3-[5-(5-phenyl-thiophen-2-yl)-1H-indol-3-yl]-propionic acid. 1H-NMR (300 MHz, CD3OD): 3.21-3.26 (m, 2H), 4.25 (q, 1H), 7.15-7.35 (m, 8H), 7.58 (d, 2H), 7.82 (d, 1H).

Workup

  1. customMicrowave vial was capped
  2. customReaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered through a syringe
  5. filtrationfilter
  6. customseparated by a reverse phase preparative-HPLC using YMC-Pack ODS 100×30 mm ID column (MeOH/H2O/TFA solvent system)
  7. concentrationThe pure fractions were concentrated in vacuum
  8. temperaturefrozen

Sources & evidence

ORD record
ord-04215f89b43c45578295bda56880a747
Source dataset
uspto-grants-2012_01
Patent number
US08093291B2

Linked notes

Loading…