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Water → tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate

HRID 634155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 634155
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2I.CN(C=O)C.C([Sn](CCCC)(CCCC)[C:29]1[N:34]=[C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=[CH:31][CH:30]=1)CCC.O>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.[Cu]I.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2[C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)[N:34]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 17749978tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylateHCID 185257394-(6-(Tributylstannyl)pyridin-2-yl)morpholine

Produkt 1

HCID 68328180tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylateAusbeute 53,13 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of Pd(PPh3)4 (255.0 mg, 220.6 μmol), tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate (1000 mg, 2369 μmol) and CuI (546.2 mg, 2868 μmol) was added DMF (12 mL) followed by 4-(6-(tributylstannyl)pyridin-2-yl)morpholine (1000 mg, 2206 μmol). The mixture was heated at 100° C. for 20 min. After cooled to RT, the reaction was added H2O (5 mL) and DCM (5 mL). The organic layer was separated. The aqueous layer was extracted with DCM (10 mL×2). The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The brown crude oil was purified with silica gel chromatography (eluting with 100% DCM) to give tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (537.3 mg, 53.13%) as a white solid. MS (ESI, pos. ion) m/z: 458 (M+1). 1H NMR (400 MHz, DMSO-d6) ppm 1.66 (s, 9H), 3.50-3.62 (m, 4H), 3.74-3.83 (m, 4H), 6.80 (d, J=8.4 Hz, 1H), 7.33 (d, J=7.4 Hz, 1H), 7.54 (dd, J=8.9, 2.1 Hz, 1H), 7.64 (dd, J=8.4, 7.6 Hz, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.29 (s, 1H), 8.68 (d, J=2.2 Hz, 1H)

Aufarbeitung

  1. temperatureAfter cooled to RT
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with DCM (10 mL×2)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe brown crude oil was purified with silica gel chromatography (eluting with 100% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-87ffd03e504a411b8a5a149f10ec4c31
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321756B2

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