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(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → (R)-tert-butyl 3-(3-(2,3-dihydrobenzofuran-5-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

HRID 1467333
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467333
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.[O:46]1[C:50]2[CH:51]=[CH:52][C:53](B(O)O)=[CH:54][C:49]=2[CH2:48][CH2:47]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>[O:46]1[C:50]2[CH:51]=[CH:52][C:53]([C:2]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]5[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]5)=[O:12])[CH:9]=4)[N:4]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:3]=3)=[CH:54][C:49]=2[CH2:48][CH2:47]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 70652333(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Produkt 1

HCID 67997292(R)-tert-butyl 3-(3-(2,3-dihydrobenzofuran-5-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate (650 mg, 1 mmol) was added to a vial containing 2,3-dihydrobenzofuran-5-ylboronic acid (180 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol). After purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 mL) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for overnight. Upon completion, the mixture was concentrated under vacuo. Water (10 mL) was added and was extracted using dichloromethane (3×25 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting suspension was filtered and concentrated. The crude product was purified using flash chromatography.

Aufarbeitung

  1. customAfter purging the vial with nitrogen gas, dioxane (3 mL) and 2M sodium carbonate (1.5 mL)
  2. additionwas added to the vial respectively
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. additionWater (10 mL) was added
  5. extractionwas extracted
  6. customdried
  7. filtrationThe resulting suspension was filtered
  8. concentrationconcentrated
  9. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-3d32aefa722d46a3a02248cbf0461f8c
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999957B2

Notizen zur Reaktion

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