Hydrochloric Acid → 3-Chloro-5-(dihydroxyboryl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646138
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C([Mg]Cl)(C)C.[Li+].[Cl-].[B:34](OCC)([O:38]CC)[O:35]CC.Cl>C1COCC1.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11]([B:34]([OH:38])[OH:35])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 433294Lithium ChlorideHCID 686997713-Chloro-5-iodo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 686978453-Chloro-5-(dihydroxyboryl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To solution of 3-chloro-5-iodo-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (1.45 g, 3.0 mmol, see step (a) above) in THF (9 mL) was added i-PrMgCl×LiCl (0.95 M solution in THF; 3.26 mL, 3.1 mmol) at −40° C. over 5 min. After stirring for 15 min at −40° C., B(OEt)3 (1.56 mL, 9.0 mmol) was added. The temperature of the reaction mixture was allowed to reach 0° C. over 2 h, then HCl (2.5 M solution in water; 3.6 mL, 36 mmol) was added and stirring continued for a further 1 h at 0° C. The reaction mixture was diluted with brine (70 mL) and extracted with t-BuOMe (4×70 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4 and concentrated. The solid thereby obtained was washed several times with light petrol and filtered affording pure sub-title compound (1.04 g, 86%)

Aufarbeitung

  1. waitto reach 0° C. over 2 h
  2. stirringstirring
  3. waitcontinued for a further 1 h at 0° C
  4. extractionextracted with t-BuOMe (4×70 mL)
  5. washThe combined organic extracts were washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe solid thereby obtained
  9. washwas washed several times with light petrol
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9011f6e8f373477593836f2eee03a1d1
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705023B2

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