HCID 21884582, compound → HCID 21884298, compound

HRID 722518Notes

Reaction equation

HRID 722518 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][C:16]=3[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])([O-])=O>O1CCOCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][C:16]=3[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 21884582HCID 21884582, compound

Product 1

HCID 21884298HCID 21884298, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared by the method of Example 15e), from palladium (10 mol %) on carbon (10 mg, 0.1 mmol) and 2-(3-nitro-4-ethoxyphenyl)-5-phenylbenzoxazole (100 mg, 0.3 mmol) in dioxane (1 ml) which gave the crude subtitle compound (51 mg, 56%) as a white solid which was sufficiently pure (by TLC and 1H NMR spectroscopy) to be used in the next step, RF(2:1 Petrol-EtOAc) 0.50; 1H NMR (CDCl3) δ 7.92(1H, d, J=1.0, Ar), 7.68–7.60(4H, m, Ar), 7.57–7.51(2H, m, Ar), 7.47(2H, brt, J=7.0 Hz, Ar), 7.36(1H, tt, J=1.0, 6.5 Hz, Ar), 6.89(1H, d, J=8.5 Hz, Ar), 4.16(2H, q, J=7.0 Hz, CH2), 3.98(2H, brs, NH2), 1.49(1H, t, J=2.5 Hz, CH3).

Sources & evidence

ORD record
ord-cef77d220aa9425a9b3c09ca603c33b4
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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