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2-Bromonaphthalene → HCID 21877272, Verbindung

HRID 1862100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1862100
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Li]CCCC.[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:39]=[C:38]3[C:34]([C:35](I)=[N:36][N:37]3[S:40]([C:43]3[C:48]([CH3:49])=[CH:47][C:46]([CH3:50])=[CH:45][C:44]=3[CH3:51])(=[O:42])=[O:41])=[CH:33][CH:32]=2)=[CH:27][C:26]=1[O:53][CH3:54])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C1COCC1.[Cl-].[Cl-].[Zn+2].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>[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:39]=[C:38]3[C:34]([C:35]([C:2]4[CH:11]=[CH:10][C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH:3]=4)=[N:36][N:37]3[S:40]([C:43]3[C:48]([CH3:49])=[CH:47][C:46]([CH3:50])=[CH:45][C:44]=3[CH3:51])(=[O:42])=[O:41])=[CH:33][CH:32]=2)=[CH:27][C:26]=1[O:53][CH3:54])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 113722-BromonaphthaleneHCID 516892Sodium BicarbonateHCID 21877467HCID 21877467, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 21877272HCID 21877272, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855
Zincchloride
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-Bromonaphthalene (117 mg, 0.564 mmol, 6.0 equiv) was dissolved in THF (0.75 mL) and cooled to −78° C. The mixture was treated with n-BuLi (226 μL, 2.5 M, 6.0 equiv) and was allowed to stir at −78° C. for 30 min. The mixture was then added to freshly dried ZnCl2 solid (139 mg, 0.80 mmol, 8.5 equiv) via cannula and the resulting mix was allowed to warm to 23° C. (during the addition the yellow color disappears). After 30 min at, 23° C. the mixture is added to a mixture of 6-(4-benzyloxy-3-methoxy-phenyl)-3-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole (60 mg, 0.094 mmol, 1 equiv) and Pd(PPh3)4 (6 mg, 0.005 mmol, 0.05 equiv) via cannula The resulting solution was allowed to stir for 16 h. Saturated sodium bicarbonate was added and the mixture was partitioned between saturated sodium bicarbonate (15 mL) and ethyl acetate (15 mL). The organic material was dried over sodium sulfate, decanted and concentrated. Purification by silica gel chromatography (1:9-2:8 ethyl acetate-hexane) gave 6-(4-benzyloxy-3-methoxy-phenyl)-3-naphthalen-2-yl-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole as a solid (42 mg, 70%): Rfsm 0.4, p 0.4 (ethyl acetate-hexane 3:7); 1H NMR (CDCl3) δ 8.44 (s, 1H), 8.41 (s, 1H), 8.12 (d, 1H, J=8 Hz), 8.05-7.00 (m, 17H), 5.30 (s, 2H), 4.02 (s, 3H), 2.80 (s, 3H), 2.34 (s, 3H).

Aufarbeitung

  1. additionthe resulting mix
  2. temperatureto warm to 23° C. (
  3. additionduring the addition the yellow color
  4. stirringto stir for 16 h
  5. customthe mixture was partitioned between saturated sodium bicarbonate (15 mL) and ethyl acetate (15 mL)
  6. dry with materialThe organic material was dried over sodium sulfate
  7. customdecanted
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (1:9-2:8 ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c79b2bdcd1fc4bc581905825ceb11d8c
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06534524B1

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