Chloroform → HCID 68521334, compound

HRID 2384520Notes

Reaction equation

HRID 2384520 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N+:6]([O-])[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[S:4][C:3]=1[S:15]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=1)(=[O:17])=[O:16].C(Cl)(Cl)Cl>C(O)(=O)C.[Fe]>[NH2:11][C:8]1[CH:9]=[C:10]2[C:2]([Br:1])=[C:3]([S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=3)(=[O:16])=[O:17])[S:4][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 68519824HCID 68519824, compound

Product 1

HCID 68521334HCID 68521334, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

3-Bromo-2-(3-cyano-5-fluoro-benzenesulfonyl)-5-nitro-thieno[2,3-b]pyridin-N-oxide (1.0 g, 2.18 mmol) was suspended in acetic acid (12 ml) and Fe powder was added (0.73 g, 13 mmol). The reaction mixture was stirred at 60-70° C. for 60 minutes. Chloroform (45 ml) was added and after filtration through celite the filtrate was evaporated, the crude residue was treated with methanol (3 ml). The product was filtered, washed with methanol. It was obtained (0.69 g, 76.7%) as a yellow powder. LC-MS: (M+H)+ 413.1.

Workup

  1. filtrationafter filtration through celite the filtrate
  2. customwas evaporated
  3. additionthe crude residue was treated with methanol (3 ml)
  4. filtrationThe product was filtered
  5. washwashed with methanol
  6. customIt was obtained (0.69 g, 76.7%) as a yellow powder

Sources & evidence

ORD record
ord-5447f3b459614853822be6549a6b67cc
Source dataset
uspto-grants-2012_09
Patent number
US08263773B2

Reaction notes

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