HCID 66779914, compound → HCID 66779799, compound

HRID 1470340Notes

Reaction equation

HRID 1470340 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[CH:21]=[C:22]([C:24]4[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=4)[O:23][C:16]=23)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[CH3:31][O:30][C:28]1[CH:29]=[C:24]([C:22]2[O:23][C:16]3[C:17](=[N:18][CH:19]=[CH:20][C:15]=3[C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=3)[CH:21]=2)[CH:25]=[C:26]([O:34][CH3:35])[C:27]=1[O:32][CH3:33]

Participants

4

Reactant 1

HCID 66779914HCID 66779914, compound

Product 1

HCID 66779799HCID 66779799, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7-(3-Benzyloxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridine (0.137 mmol) is dissolved in THF (10 ml) and Pd—C 5% (0.2 g) is added, and the compound is hydrogenated 2 days at room temperature. The reaction solution is filtered and the filtrate removed in vacuo. The precipitate is suspended in diethylether and filtrated. The product is obtained after drying at 40° C. for 4 h as yellow solid (23 mg, 44%); HPLC (method A): Rt 2.55 min (purity 99.2%); LCMS (ESI+) (method E): Rt 1.995 min, M+H+ 378.1 m/z; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 9.73 (s, 1H), 8.54 (d, J=5.1, 1H), 7.72 (s, 1H), 7.60-7.55 (m, 1H), 7.55-7.48 (m, 2H), 7.42 (t, J=7.9, 1H), 7.32 (s, 2H), 6.96-6.91 (m, 1H), 3.91 (s, 6H), 3.74 (s, 3H).

Workup

  1. filtrationThe reaction solution is filtered
  2. customthe filtrate removed in vacuo
  3. filtrationfiltrated
  4. customThe product is obtained
  5. dry with materialafter drying at 40° C. for 4 h as yellow solid (23 mg, 44%)

Sources & evidence

ORD record
ord-c662c1ce7079432a9f17ed4b0cb6c090
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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