N-(2-aminophenyl)-2-(1-ethyl-6-fluoro-4-hydroxy-1-H-indol-3-yl) acetamide → 3-((1H-benzo[d]imidazol-2-yl)methyl)-1-ethyl-6-fluoro-1H-indol-4-ol

HRID 1404102Notes

Reaction equation

HRID 1404102 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([F:21])=[CH:17][C:18]=2[OH:20])[N:13]([CH2:22][CH3:23])[CH:12]=1>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[CH2:10][C:11]1[C:19]2[C:18]([OH:20])=[CH:17][C:16]([F:21])=[CH:15][C:14]=2[N:13]([CH2:22][CH3:23])[CH:12]=1

Participants

3

Reactant 1

HCID 68322751N-(2-aminophenyl)-2-(1-ethyl-6-fluoro-4-hydroxy-1-H-indol-3-yl) acetamide

Product 1

HCID 672349353-((1H-benzo[d]imidazol-2-yl)methyl)-1-ethyl-6-fluoro-1H-indol-4-olYield 23.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The solution of 12-2 (0.3 g, 0.92 mmol) in 25 mL of acetic acid was heated to 80° C. for 8 h. The volatile was removed in vacuo and the residue was neutralized with Na2CO3 solution to pH:7. The mixture was extracted with ethyl acetate (100 mL) and washed with brine. The organic layer was dried over anhydrous Na2SO4. After filtration and concentration, a residue was obtained, which was purified by preparative TLC to give 12-3 (68 mg, 23.9%)

Workup

  1. customThe volatile was removed in vacuo
  2. extractionThe mixture was extracted with ethyl acetate (100 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customa residue was obtained
  7. customwhich was purified by preparative TLC

Sources & evidence

ORD record
ord-7462634bb35a4874b986e0085226df60
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

Loading…