Potassium Carbonate → [3-(2-Methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-indol-1-yl]-acetic acid

HRID 750640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750640
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]2[CH3:20])=[CH:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30]>CN(C=O)C.CCOC(C)=O>[CH3:20][N:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]1[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:28][C:29]([OH:31])=[O:30])[CH:2]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 533485243-(1H-Indol-3-yl)-2-methyl-2,3-dihydro-isoindol-1-one

Produkt 1

HCID 59753826[3-(2-Methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-indol-1-yl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The product from example 20, step b) (450 mg, 1.72 mmol) was dissolved in DMF and treated with K2CO3 (284 mg, 2.06 mmol) followed by t-butyl bromoacetate (255 μL, 1.72 mmol). The reaction was heated to 100° C. for 5 h. The reaction was cooled, diluted with EtOAc, washed 3 times with water, and concentrated. The crude product was treated with TFA (neat) at room temperature for 45 minutes. The reaction was then concentrated to dryness and purified by preparative LCMS to give the title compound. 1H NMR (CD3OD) δ 7.74-7.78 (m, 1H), 7.43 (t, J=3.7 Hz, 1H), 7.41 (t, J=3.6 Hz, 1H), 7.36 (s, 1H), 7.28-7.31(m, 1H), 7.20 (d, J=8.1 Hz, 1H), 6.96 (t, J=7.2 Hz, 1H), 6.67 (t, J=7.2 Hz, 1H), 6.48 (d, J=7.8 Hz, 1H), 4.62 (s, 2H), 2.78 (s, 3H); MS: ESI (negative): 319 (M−H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. washwashed 3 times with water
  3. concentrationconcentrated
  4. additionThe crude product was treated with TFA (neat) at room temperature for 45 minutes
  5. concentrationThe reaction was then concentrated to dryness
  6. custompurified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-4897a98679324da1bedf40c8238ef661
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405215B2

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