Formic Acid → 6-Bromo-1-(oxan-4-yl)-1H-benzimidazole

HRID 1051531Notes

Reaction equation

HRID 1051531 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=1.[CH:18](O)=O>CO.[Fe]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]=[CH:18][N:8]([CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 65341357HCID 65341357, compound

Product 1

HCID 529880396-Bromo-1-(oxan-4-yl)-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(5-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-amine (600 mg, 1.99 mmol) in HCOOH (10 mL) was added Fe powder (1.3 g, 23.2 mmol). After stirring for 4 h at reflux temperature, the mixture was diluted with MeOH (100 mL) and filtered over a Celite pad. The filtrate was concentrated to give the title compound which was directly used for next step without further purification.

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered over a Celite pad
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ffe7f98e938d4b32a8cee6c3e2683d21
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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