Ethanol → racemic cis-2-[1-(4-Bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]cyclohexanecarboxylic acid

HRID 2178425Notes

Reaction equation

HRID 2178425 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][C:9]=2[N+:26]([O-])=O)=[CH:4][CH:3]=1.[OH2:31].O.[Sn](Cl)Cl.[CH2:36]([OH:38])[CH3:37]>>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[N:17]=4)=[CH:10][C:9]=3[N:26]=[C:5]2[C@H:4]2[CH2:3][CH2:2][CH2:30][CH2:29][C@H:37]2[C:36]([OH:31])=[O:38])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 90414040N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

Product 1

HCID 86281518racemic cis-2-[1-(4-Bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]cyclohexanecarboxylic acidYield 54%

Conditions

Temperature
80 °C

Procedure

To a 1 L round-bottomed flask were added a stir bar, N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline (6.1 g, 13 mmol), tin(II) chloride dihydrate (12.5 g, 55.4 mmol) and ethanol (250 mL). The resulting mixture was heated to 80° C. After 24 h, the mixture was cooled and partitioned between water (100 mL) and EtOAc (300 mL). The mixture was stirred vigorously while the pH was adjusted to 8 using 2 M sodium carbonate. The organic layer was separated and washed with brine (100 mL), dried with magnesium sulfate, filtered, and concentrated to dryness to afford the title compound (3.1 mg, 54%). The residue was kept under vacuum until use.

Workup

  1. additionTo a 1 L round-bottomed flask were added a stir bar
  2. temperaturethe mixture was cooled
  3. custompartitioned between water (100 mL) and EtOAc (300 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fe1aae63ecdc49aeafb9412b03e2e726
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

Loading…