HCID 56849421, compound → HCID 66779373, compound

HRID 1470349Notes

Reaction equation

HRID 1470349 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>CO.N.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[CH2:25][NH2:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 56849421HCID 56849421, compound

Product 1

HCID 66779373HCID 66779373, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

3-[2-(3,4,5-Trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzonitrile (0.067 mmol) is dissolved in methanol/NH3 (10%, 10 ml) and sponge nickel catalyst (70%, 0.1 g) is added. The mixture is hydrogenated at 5.6 bar at 50° C. for 15 h. The suspension is filtrated and the solvent removed in vacuo. The precipitate is suspended in diethylether and filtrated. The product is obtained after drying in vacuo as slight green solid (67% yield). HPLC (method A): Rt 2.41 min (purity 97.3%); LCMS (ESI+) (method E): Rt 1.527 min, M+H+ 391.1 m/z; 1H NMR (400 MHz, DMSO-d6) δ [ppm] 8.56 (d, J=4.8, 1H), 8.25 (s, 1H), 7.93 (d, J=7.1, 1H), 7.74 (s, 1H), 7.65-7.45 (m, 3H), 7.34 (s, 2H), 3.92 (s, 6H), 3.88 (s, 2H), 3.81-3.68 (m, 5H).

Workup

  1. filtrationThe suspension is filtrated
  2. customthe solvent removed in vacuo
  3. filtrationfiltrated
  4. customThe product is obtained

Sources & evidence

ORD record
ord-b734f1b9d98a4fe7883e40b68cb1168c
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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