HCID 56849420, compound → HCID 68083685, compound

HRID 1470351Notes

Reaction equation

HRID 1470351 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:16]=[C:17]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[O:18][C:11]=23)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1COCC1.[Pd]>[CH3:26][O:25][C:23]1[CH:24]=[C:19]([C:17]2[O:18][C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:10]=3[C:6]3[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=3)[CH:16]=2)[CH:20]=[C:21]([O:29][CH3:30])[C:22]=1[O:27][CH3:28]

Participants

4

Reactant 1

HCID 56849420HCID 56849420, compound

Product 1

HCID 68083685HCID 68083685, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7-(3-Nitro-phenyl)-2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridine (0.121 mmol) is dissolved in THF (10 ml) and Pd—C 5% (0.2 g) is added and the reaction is hydrogenated 16 h at RT. The mixture is filtered and the filtrate removed in vacuo. The precipitate is suspended in diethylether and filtrated. The product is obtained after reversed phase column chromatography as yellow solid in a yield of 27%. HPLC (method A): Rt 2.45 min (purity 99.2%); LCMS (ESI+) (method E): Rt 1.89 min, M+H+ 377.1 m/z; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 8.60 (d, J=5.3, 1H), 7.80 (s, 1H), 7.71-7.55 (m, 2H), 7.51-7.33 (m, 4H), 6.97 (d, J=6.9, 1H), 4.42 (s, br, 2H), 3.93 (s, 6H), 3.75 (s, 3H).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate removed in vacuo
  3. filtrationfiltrated
  4. customThe product is obtained after reversed phase column chromatography as yellow solid in a yield of 27%

Sources & evidence

ORD record
ord-1688c45b72994ed5856ad4850bbc25b7
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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