Hydrochloric Acid → [3-(Biphenyl-4-ylsulfanyl)-5-fluoro-2-methyl-indol-1-yl]-acetic Acid

HRID 18495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18495
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.II.Cl>CN(C=O)C.O>[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][C:19]([S:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[CH3:15])=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 27604144-Phenylbenzene-1-thiolHCID 674666192(5-fluoro-2-methyl-1H-indol-1-yl)acetic acid

Produkt 1

HCID 23624516[3-(Biphenyl-4-ylsulfanyl)-5-fluoro-2-methyl-indol-1-yl]-acetic AcidAusbeute 0 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (5-fluoro-2-methyl-indol-1-yl)-acetic acid (0.5 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight the mixture was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.1 μg).

Aufarbeitung

  1. extractionthe organics extracted with EtOAc
  2. extractionThe EtOAc extractions
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give crude material
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-0af3edcd23204d618582a3bfe22d3955
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741360B2

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