Sodium Carbonate → 7-[(1E)-3-(diethylamino)prop-1-enyl]-3-(4-phenoxyphenyl)isoxazolo[4,5-c]pyridin-4-amine

HRID 17246

Reaktionsgleichung

Reaktionsgleichung von HRID 17246
I[C:2]1[C:3]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1.C(OC(OCC)/C=C/B1OC(C)(C)[C:33]([CH3:39])([CH3:38])O1)C.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[CH2:5]([N:6]([CH2:7][CH3:2])[CH2:39]/[CH:33]=[CH:38]/[C:2]1[C:3]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1)[CH3:4]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 11065022(E)-2-(3,3-Diethoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 184508777-Iodo-3-(4-phenoxyphenyl)isoxazolo[4,5-c]pyridin-4-amine

Produkt 1

HCID 184508637-[(1E)-3-(diethylamino)prop-1-enyl]-3-(4-phenoxyphenyl)isoxazolo[4,5-c]pyridin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

7-Iodo-3-(4-phenoxyphenyl)isoxazolo [4,5-c]pyridin-4-amine (0. 100 g, 0.233 mmol) in 1,2-dimethoxyethane (4 mL) and water (2 mL) was reacted with an 2-[(E)-3,3-diethoxy-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.09 g, 0.35 mmol), sodium carbonate (0.05 g, 0.47 mmol) and tetrakis triphenylphosphine palladium (0) (0.02 g, 0.014 mmol) at 90° C. for 18 hours. The solvent was removed in vacuo and the residue was dissolved in acetone/water 95:5 (10 mL) then p-toluene sulfonic acid was added. The mixture was stirred at ambient temperature for 18 hours then evaporated and the residue dissolved in 1,2-dichloroethane (4 mL). Diethylamine (100 mg) was added followed by sodium triacetoxyborohydride (100 mg). The mixture was stirred for 18 hours then the concentrated and by preparative RP-HPLC (Rainin C18, 8 mm, 100 Å, 25 cm; 20% acetonitrile—-0.1M ammonium acetate isocratic for 5 minutes, then 20-80% acetonitrile—0.1M ammonium acetate over 30 min, 21 ml/min) followed by treatment with Silica-carbonate and lyophilization: 1H NMR (DMSO-d6, 400 MHz) δ8.08 (s, 1H), 7.7 (d, 2H), 7.46 (t, 2H), 7.16-7.25 (m, 5H), 6.6 (d, 1H), 6.49 (m, 1H), 6.33 (bs, 2H), 3.25 (d, 2H), 2.50 (q, 4H), 1.0 (t, 6H); Rt=2.90 min (Conditions a), MS m/e: 413 (M−H)−.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in acetone/water 95:5 (10 mL)
  3. additionp-toluene sulfonic acid was added
  4. customthen evaporated
  5. dissolutionthe residue dissolved in 1,2-dichloroethane (4 mL)
  6. additionDiethylamine (100 mg) was added
  7. stirringThe mixture was stirred for 18 hours
  8. concentrationthe concentrated and by preparative RP-HPLC (Rainin C18, 8 mm, 100 Å, 25 cm
  9. wait20% acetonitrile—-0.1M ammonium acetate isocratic for 5 minutes
  10. wait20-80% acetonitrile—0.1M ammonium acetate over 30 min

Quellen und Nachweise

ORD-Eintrag
ord-f8f9cec52495405baeebfe1405e7d4b5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737160B2

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