Sodium Carbonate → Methyl 2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 860731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860731
C([O-])([O-])=O.[Na+].[Na+].[CH:7]1([C:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=3)[NH:15][C:14]=2B2OC(C)(C)C(C)(C)O2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:35]([O:42][C:43]1[C:48](Br)=[CH:47][CH:46]=[CH:45][N:44]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Li+].[Cl-]>C(O)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>[CH2:35]([O:42][C:43]1[C:48]([C:14]2[NH:15][C:16]3[C:21]([C:13]=2[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:17]=3)=[CH:47][CH:46]=[CH:45][N:44]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 147124562-Benzyloxy-3-bromopyridineHCID 23152432methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate

Produkt 1

HCID 58765212Methyl 2-(2-(benzyloxy)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylateAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2M Na2CO3 (1.25 mL, 2.5 mmol) aqueous solution was added to a suspension of methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate (383 mg, 1.0 mmol), 2-(benzyloxy)-3-bromopyridine (317 mg, 1.2 mmol) and LiCl (84.8 mg, 2.0 mmol), in ethanol (3 mL) and toluene (3 mL). The mixture was degassed by evacuating the reaction flask and then flushing with N2. Pd(PPh3)4 (58 mg, 0.05 mmol) was then added, and the reaction mixture was heated at 80° C. for 6 hr. The reaction mixture was then filtered and concentrated in vacuo, and the resultant residue was purified by silica gel flash chromotagraphy using hexanes to 50% ethyl acetate in hexanes as eluent to afford the title compound as a yellowish solid, (310 mg, 70% yield). MS m/z 441(MH+); 1H NMR (500 MHz, CDCl3) δ ppm 1.32–1.46 (m, 3 H) 1.78–1.93 (m, 5 H) 2.05–2.16 (m, 2 H) 2.96 (m, 1 H) 3.92 (s, 3 H) 5.25 (s, 2 H) 6.39 (t, J=6.87 Hz, 1 H) 7.31–7.41 (m, 6 H) 7.60 (dd, J=7.17, 1.98 Hz, 1 H) 7.71 (d, J=8.55 Hz, 1 H) 7.84 (d, J=8.55 Hz, 1 H) 8.07 (s, 1 H) 10.32 (s, 1 H).

Aufarbeitung

  1. customThe mixture was degassed
  2. customby evacuating the reaction flask
  3. customflushing with N2
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated in vacuo
  6. customthe resultant residue was purified by silica gel flash chromotagraphy

Quellen und Nachweise

ORD-Eintrag
ord-86a033d247de4feda94217aa3f7cf7ce
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153848B2

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