HCID 21474190, compound → HCID 21474161, compound

HRID 2294163Notes

Reaction equation

HRID 2294163 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[C:20]5[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=5[N:18]=[CH:17]4)[CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>[Pd].C(O)C>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[C:20]5[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=5[N:18]=[CH:17]4)[CH:14]=3)[NH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 21474190HCID 21474190, compound

Product 1

HCID 21474161HCID 21474161, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(3-(cyclohexen-1-yl)indol-5-yl)-5-methylbenzimidazole (0.110 g, 0.34 mmol), 10% Pd on carbon (0.027 g), and absolute ethanol (2 mL) was shaken under an atmosphere of hydrogen (3 atm) for 72 hours. The resulting reaction mixture was filtered through Celite®, and the filtrate was evaporated under reduced pressure to afford the title compound (0.090 g, 80%) as a dark brown foam. Mp, decomposes 120° C.; 1H NMR (DMSO-d6) d 11.5 (br s, NH), 8.41 (s, 1H), 7.73 (s, 1H), 7.56-7.52 (m, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.27-7.24 (m, 2H), 7.13 (d, J=8.0 Hz, 1H), 2.88-2.75 (m, 1H), 2.45 (s, 3H), 2.10-1.60 (m, 10 H); IR (KBr) 2924, 2851, 1612, 1580, 1492, 1447 cm-1 ; FAB LRMS (m/z, relative intensity) 331 (25), 330 ([MH]+, 100). HRMS calculated for C22 H23N3 : 329.1887. Found: 329.1874.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through Celite®
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-da38f9f1358340b093940eb23f2c864e
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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