Nitric Acid → HCID 68519824, compound

HRID 2384519Notes

Reaction equation

HRID 2384519 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N+:6]([O-:11])[CH:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[S:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=1)(=[O:14])=[O:13].[N+:24]([O-])([OH:26])=[O:25].CCOCC>C(O)(=O)C>[Br:1][C:2]1[C:10]2[C:5](=[N+:6]([O-:11])[CH:7]=[C:8]([N+:24]([O-:26])=[O:25])[CH:9]=2)[S:4][C:3]=1[S:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 68439065HCID 68439065, compound

Product 1

HCID 68519824HCID 68519824, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Bromo-2-(3-cyano5-fluorobenzenesulfonyl)-thieno[2,3-b]pyridin-N-oxide (prepared as described in WO 2007/072095) (7.97 g, 19.3 mmol) was boiled at 120° C. with 66% nitric acid (1.22 ml) in acetic acid (25 ml) for 4 hours. The reaction mixture was evaporated and the residue was purified by chromatography (Kieselgel 60, chloroform:methanol=5:0.1). First the starting material was isolated (3.7 g, 47%), than a yellow solid, which was treated with ether (5 ml). After filtration the title compound was isolated (0.72 g, 8.3%). LC-MS: (M+H)+ 459.1.

Workup

  1. customfor 4 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by chromatography (Kieselgel 60, chloroform:methanol=5:0.1)
  4. customFirst the starting material was isolated (3.7 g, 47%)
  5. filtrationAfter filtration the title compound
  6. customwas isolated (0.72 g, 8.3%)

Sources & evidence

ORD record
ord-70eaff1d157a4bf2b182a854d392d43a
Source dataset
uspto-grants-2012_09
Patent number
US08263773B2

Reaction notes

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