Sodium Bicarbonate → HCID 131732441, compound

HRID 1848741Notes

Reaction equation

HRID 1848741 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=2[N+:16]([O-])=O)=[C:4]([F:22])[CH:3]=1.C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:5]([CH2:6][NH:7][C:8]2[C:9]([NH2:16])=[CH:10][CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)=[C:4]([F:22])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 90410235HCID 90410235, compound

Product 1

HCID 131732441HCID 131732441, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(4-bromo-2,6-difluorobenzyl)-5-methoxy-2-nitroaniline (600 mg, 1.61 mmol) in EtOH (100 mL) was added SnCl22H2O (1.8 g, 8.1 mmol). The mixture was heated at 100° Celsius for 16 h. The mixture was cooled to RT and NaHCO3 (200 mL) was added. The mixture was filtered through celite and the filtrate extracted with EtOAc (3×200 mL). The combine organics were concentrated to dryness to provide the title compound which was used in the next step without further purification. MS (ESI): mass calcd. for C14H13BrF2N2O, 342.02; m/z found, 343.1 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe mixture was filtered through celite
  3. extractionthe filtrate extracted with EtOAc (3×200 mL)
  4. concentrationThe combine organics were concentrated to dryness

Sources & evidence

ORD record
ord-d8a45ed8084e423a976c4a6b0ac131c0
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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