HCID 58413845, compound → HCID 67173701, compound

HRID 1256068Notes

Reaction equation

HRID 1256068 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11]([NH:14][C:15]1[C:16]([F:25])=[CH:17][C:18]2[CH2:22][O:21][B:20]([OH:23])[C:19]=2[CH:24]=1)(=[O:13])=[O:12]>CC(O)=O.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11]([NH:14][C:15]2[C:16]([F:25])=[CH:17][C:18]3[CH2:22][O:21][B:20]([OH:23])[C:19]=3[CH:24]=2)(=[O:12])=[O:13])=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 1

HCID 58413845HCID 58413845, compound

Product 1

HCID 67173701HCID 67173701, compoundYield 7.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-chloro-N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzenesulfonamide (0.5 g, 1.3 mmol), iron powder (0.36 g, 6.5 mmol) in AcOH (10 mL) was heated to 50° C. over night and monitored by LC/MS. The mixture was filtered, washed with EtOAc then AcOH, and evaporated under vacuum. Preparative HPLC was applied for the purification and give title product as yellow powder yield 36.3 mg (2%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.71 (s, 1H), 7.64 (d, J=8 Hz, 1H), 7.44 (d, J=8.8 Hz, 1H), 7.20 (d, J=10 Hz, 1H), 6.65 (d, J=2 Hz, 1H), 6.41 (dd, J=8.8, 2.4 Hz, 1H), 4.88 (s, 2H); MS (ESI): m/z=355.0 (M−H, negative).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with EtOAc
  3. customAcOH, and evaporated under vacuum
  4. customPreparative HPLC was applied for the purification

Sources & evidence

ORD record
ord-3e5c7fcbfe884b3a8175776a832d0907
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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