HCID 58545582, Verbindung → 2-[5-(6-{2-[pyrrolidin-2-yl]-3H-imidazol-4-yl}-benzo[1,2-b:4,5-b']dithiophene-2-yl)-1H-imidazol-2-yl]-pyrrolidine

HRID 72031

Reaktionsgleichung

Reaktionsgleichung von HRID 72031
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]2=[CH:11][C:12]3[CH:16]=[C:15]([Sn](CCCC)(CCCC)CCCC)[S:14][C:13]=3[CH:30]=[C:8]2[CH:7]=1)CCC.C(OC([N:46]1[CH2:50][CH2:49][CH2:48][CH:47]1[C:51]1[N:52](COCC[Si](C)(C)C)[CH:53]=[C:54](Br)[N:55]=1)=O)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:46]1[CH2:50][CH2:49][CH2:48][CH:47]1[C:51]1[NH:55][C:54]([C:15]2[S:14][C:13]3[CH:30]=[C:8]4[CH:7]=[C:6]([C:54]5[NH:55][C:51]([CH:47]6[CH2:48][CH2:49][CH2:50][NH:46]6)=[N:52][CH:53]=5)[S:10][C:9]4=[CH:11][C:12]=3[CH:16]=2)=[CH:53][N:52]=1

Komponenten

5

Edukt 2

HCID 58545582HCID 58545582, VerbindungHCID 666201592-[4-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 666207262-[5-(6-{2-[pyrrolidin-2-yl]-3H-imidazol-4-yl}-benzo[1,2-b:4,5-b']dithiophene-2-yl)-1H-imidazol-2-yl]-pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Pd(PPh3)4 (61 mg, 0.053 mmol) was added to a degassed solution of 2,6-bis(tri-n-butylstannyl)-benzo[1,2-b:4,5-b′]dithiophene (202 mg, 0.26 mmol) and 2-[4-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (260 mg, 0.58 mmol) in toluene (4 mL). The reaction was refluxed for 24 hours, then cooled to room temperature and filtered through CELITE and a palladium scavenging column (Stratospheres™ PL-Guanidine MP SPE+, Part #: PL3514-CM89). The solids were rinsed twice with toluene. The filtrate was concentrated and the crude product purified by flash chromatography to yield the desired, fully protected product (100 mg, 41%). LCMS-ESI+: calculated for C46H68N6O6S2Si2: 920.42; observed [M+1]+: 921.45.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 24 hours
  2. filtrationfiltered through CELITE
  3. washThe solids were rinsed twice with toluene
  4. concentrationThe filtrate was concentrated
  5. customthe crude product purified by flash chromatography
  6. customto yield the

Quellen und Nachweise

ORD-Eintrag
ord-cc8a82c36ca24ed28d14fe7d95d786c2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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